The Ultimate 14-Day Boston to Maine Road Trip Itinerary

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Ready for an epic adventure from Boston all the way up to the stunning coast of Maine? Buckle up, because this road trip itinerary is packed with coastal charm and jaw-dropping scenery.

As a Bostonian, I’ve explored every nook and cranny of the northeast. And out of the 60+ countries I’ve visited, this coastal route in Maine is one of the nicest road trips I’ve ever done!

Starting in Boston, you’ll dive into a city brimming with history and culture—think Freedom Trail and Fenway Park. Then, I’ll guide you through scenic coastal roads where you’ll discover charming seaside towns, enjoy the freshest seafood, and even spot a lighthouse or two.

Ready to discover the rugged beauty of Maine? I’ve mapped out the must-see spots and hidden gems, making sure you get the most out of your 14 days on the road. Whether you’re a history buff, nature lover, or foodie, this ultimate guide will help you make the most of your Maine road trip itinerary, providing insider tips along the way.

Planning the Best Boston to Maine Road Trip

In 14 days, you can savor the best seafood in Portland, hike the breathtaking trails in Acadia National Park, and discover hidden gems in charming towns like Kennebunkport and Camden.

Don’t have two weeks to spare? Even just 3-4 days will give you a solid taste of Maine! The road trip from Boston to Bar Harbor (Acadia National Park) is approximately 280 miles and typically takes about 5-6 hours of driving time without stops. So, if you’re cool with jumping from town to town in a short period of time, a shorter road trip is totally doable!

Below is everything you’ll need for an amazing Boston to Maine road trip in 2024. I’ve got a detailed road trip map, a 14-day itinerary, top destinations for each stop, and essential trip-planning tips to ensure you have the best experience possible.

Road Trip Itinerary Map for Boston to Maine

Days 1-2: Boston, Massachusetts

Welcome to Boston, one of the most beautiful places in Massachusetts that feels more European than American in many ways. The cobblestone streets, classic architecture, and lively pub scene feel like Dublin or London. It’s where old meets new in the most amazing way possible (though as a Bostonian, I may be a bit biased!).

Starting your road trip in Boston is the perfect way to kick off your journey to Maine. Boston’s convenient location, accessibility, and rich history make it an ideal starting point. Logan International Airport is a major hub, offering numerous flights, rental car options, and easy access to downtown Boston.

Known for its pivotal role in the American Revolution, Boston offers a mix of historical landmarks, cultural hotspots, and fantastic food. Whether you’re wandering the red-brick neighborhoods or indulging in a bowl of clam chowder, there’s no shortage of things to see and do.

Here are my top recommendations for a memorable two days in Boston:

• Freedom Trail: This 2.5-mile-long path takes you through 16 historical sites, including the Boston Common, Paul Revere’s House, and the Old North Church. Perfect for history lovers!
• Fenway Park: If you’re a baseball fan, catch a Red Sox game at Fenway Park, one of the oldest and most beloved ballparks in the country. Even if you’re not a sports enthusiast, the atmosphere is electric and quintessentially Boston.
• Faneuil Hall and Quincy Market: Great spots for shopping, eating, and people-watching. Try the lobster rolls at the market. And don’t miss the street performers here!
• Boston Common & Public Garden: Enjoy a stroll through the oldest public park in the U.S. and the adjacent, beautifully landscaped Public Garden. Take a swan boat ride or just enjoy a leisurely stroll. In the spring, the gardens are bursting with tulips and other blooms.
• Newbury Street: This street is lined with boutique shops, cafes, and art galleries. A great place for a relaxed afternoon of exploring.
• Museum of Fine Arts: Spend a few hours at the Museum of Fine Arts, one of the largest art museums in the country. The vast collection ranges from ancient Egyptian artifacts to contemporary art.

More Attractions to See in Boston

• North End: Boston’s Little Italy is packed with amazing restaurants. Don’t miss out on Mike’s Pastry or Modern Pastry for some of the best cannolis in town. Here are my favorite activities in the North End!
• Harvard University: Take a short drive to Cambridge and wander around Harvard’s beautiful campus. The Harvard Museum of Natural History is also worth a visit.
• Boston Harborwalk: A public walkway that follows the edge of piers, wharves, beaches, and shoreline around Boston Harbor. It’s a great way to see the city from a different perspective.
• Beacon Hill: Wander the charming, cobblestone streets of Beacon Hill, known for its Federal-style rowhouses, gaslit streets, and boutique shops. Acorn Street, in particular, is one of the most photographed streets in the U.S. The historic charm and picturesque scenes make it a must-visit.

Parking in Boston can be tricky and expensive. Consider using public transportation or parking in a garage outside the city and taking the T (Boston’s subway system) into downtown. If you’re renting a car, try to pick it up at the end of your stay in Boston to avoid hefty parking fees. Most of Boston’s top attractions are easily accessible by foot or public transit.

Day 3: Salem, Massachusetts

After soaking in the history and charm of Boston, head north to Salem, Massachusetts, a town famous for its 1692 witch trials and rich maritime history. Just a 40-minute drive from Boston, it’s one of my favorite day trips on the North Shore. Salem offers a fascinating blend of historical intrigue and coastal beauty, making it the perfect stop on your road trip to Maine!

The town is brimming with museums, historic sites, and eerie attractions related to the infamous witch trials. However, Salem also boasts beautiful coastal views, charming streets, and a lively arts scene. Visiting Salem allows you to delve into a unique chapter of American history while enjoying a picturesque New England town.

Here are my top picks for things to do in Salem:

• Salem Witch Museum: Start your visit with the Salem Witch Museum to get an in-depth look at the witch trials of 1692. The museum offers dramatic exhibits and presentations that provide a detailed and engaging overview of this dark period in history.
• The House of the Seven Gables: Visit this historic mansion dating back to 1668, which was the inspiration for Nathaniel Hawthorne’s famous novel. The guided tour offers a peek into the life of a wealthy maritime family in the 1600s.
• Salem Maritime National Historic Site: Take a walk along the waterfront and explore historic buildings, wharves, and the replica tall ship Friendship of Salem. It’s a great place to learn about Salem’s role in early American trade and exploration.
• Peabody Essex Museum: This museum features an impressive collection of art and cultural artifacts from around the world. The maritime and Asian art collections are particularly noteworthy.
• Witch House: Also known as the Jonathan Corwin House, this is the only structure still standing in Salem with direct ties to the witch trials. The guided tours are very informative.
• Salem Witch Trials Memorial: A somber and reflective place, this memorial honors the victims of the 1692 witch trials. It’s a simple yet powerful tribute.
• Pickering Wharf: Stroll around this charming marina area filled with shops, restaurants, and beautiful views of the water.
• Bewitched Statue: A fun photo op, this statue of Samantha from the TV show “Bewitched” is a quirky nod to Salem’s pop culture connection.
• Salem Willows: This waterfront park is perfect for a relaxed afternoon. Enjoy the arcades, a picnic by the sea, or some local seafood.

Visiting Salem in October

Visiting Salem in October is an experience like no other. The city transforms into a Halloween wonderland with its month-long Haunted Happenings festival. You can expect haunted houses, ghost tours, parades, and themed events all over town. The energy is electric, and the streets are filled with costumed revelers, making it a fun and festive atmosphere.

Insider Tip: Since October is the busiest time of year in Salem, plan your visit well in advance. Book your accommodations early, and consider purchasing tickets for popular events and tours ahead of time to avoid long lines. Be prepared for crowds, especially on weekends, and wear comfortable shoes for walking around the city.

From the haunting tales of the witch trials to the serene beauty of the waterfront sites, Salem offers a unique blend of the eerie and the enchanting. It’s a must-visit destination on your Boston to Maine road trip that I recommend for everyone!

Day 4: Rockport and Gloucester

As you continue your road trip from Boston to Maine, spend your day exploring the charming coastal towns of Rockport and Gloucester. Just a 30-min drive from Salem, these neighboring towns on Cape Ann offer stunning seascapes, historic sites, and vibrant arts communities.

Rockport and Gloucester are quintessential New England seaside towns, each with its unique charm. Rockport is known for its picturesque harbor, art galleries, and quaint shops, while Gloucester boasts a rich maritime history, beautiful beaches, and excellent seafood. Let’s dive into some fun ideas for each.

Rockport:

• Motif No. 1 in Rockport: Start your day in Rockport by visiting Motif No. 1, the iconic red fishing shack that is one of the most painted buildings in America. Located in Rockport Harbor, it’s a great spot for photography and a symbol of the town’s artistic heritage. Capturing the perfect shot of Motif No. 1 was a highlight of my visit.
• Bearskin Neck: Wander down Bearskin Neck, a narrow peninsula lined with charming shops, art galleries, and eateries. It’s a great place to shop for unique souvenirs, enjoy a coffee, and take in the coastal views. I loved exploring the eclectic mix of shops and finding one-of-a-kind treasures.
• Halibut Point State Park: Just a short drive from Rockport, Halibut Point State Park offers scenic hiking trails with breathtaking views of the Atlantic Ocean. The park’s rocky shoreline and old granite quarry are perfect for exploration and photography. The panoramic ocean views from the park’s trails are absolutely stunning.

Gloucester:

• Gloucester’s Fishermen’s Memorial: In Gloucester, visit the Fishermen’s Memorial, also known as “The Man at the Wheel,” a poignant tribute to the town’s maritime heritage and those lost at sea. The memorial’s location along the waterfront provides a serene and reflective atmosphere.
• Cape Ann Museum: Dive into the region’s history and art at the Cape Ann Museum in Gloucester. The museum features exhibits on the area’s fishing industry, maritime art, and local artists, including Fitz Henry Lane. The museum’s rich collection gave me a deeper appreciation for Cape Ann’s cultural heritage.
• Whale Watching Tour: Gloucester is a prime spot for whale watching. Book a tour with one of the local operators to experience the thrill of seeing whales, dolphins, and other marine life up close. The excitement of spotting whales in their natural habitat was an unforgettable experience.
• Good Harbor Beach: Relax and unwind at Good Harbor Beach, one of Gloucester’s most beautiful sandy beaches. It’s a great place for swimming, sunbathing, and taking a leisurely walk along the shore. This is my favorite beach on the North Shore! I recommend a couple of hours here, preferably in the afternoon (parking is free after 5pm).

Enjoy fresh seafood at local spots like Roy Moore Lobster Co. in Rockport and The Gloucester House (Blue Collar Lobster) in Gloucester. The lobster rolls and clam chowder are some of the best I’ve ever had.

Both towns can get busy, especially during the summer months. Arrive early to find convenient parking, and consider using public parking lots.

Addition Itinerary Suggestion: Newburyport, MA

Newburyport is a place I visit often and recommend to everyone on the way to Maine. Here’s why you should spend a few hours in this hidden gem before continuing on your road trip.

Key Attractions and Activities in Newburyport

• Downtown Newburyport: Stroll through the picturesque downtown area, filled with unique shops, art galleries, and cozy cafes. The historic architecture and vibrant street life make it a perfect place for a leisurely walk.
• Waterfront Park: Enjoy the scenic views of the Merrimack River at Waterfront Park. It’s a great spot for a picnic, a relaxing walk, or simply sitting and watching the boats go by. The park’s tranquil ambiance is perfect for unwinding.
• Custom House Maritime Museum: Dive into Newburyport’s rich maritime history at this fascinating museum. The exhibits cover the town’s shipbuilding past, maritime trade, and local history.
• Michael’s Harborside: For a memorable dining experience, head to Michael’s Harborside, a popular restaurant right on the water. Enjoy fresh seafood dishes while taking in stunning views of the harbor. The lobster bisque and outdoor seating with ocean views make it a standout.

Take in the beautiful brick architecture and waterfront promenade, and afterwards, don’t miss nearby Plum Island. This barrier beach island is located off the shore of Newburyport, and it’s the perfect place to spend an hour or two before continuing northward!

Day 5: Portsmouth, New Hampshire

Next, make your way to Portsmouth, New Hampshire, one of the top places to live and visit in New England. This vibrant, historic town is just an hour’s drive from Rockport and Gloucester, and 30 minutes from Newburyport. Portsmouth is a fantastic place to explore, offering rich history, amazing food, and scenic walks along cobblestone streets and the Piscataqua River.

Portsmouth’s compact and walkable downtown and bustling waterfront make it an awesome stop. It also has some of the best restaurants on the East Coast, especially if you like seafood! Here are a few experiences I recommend.

Top Attractions in Portsmouth, NH:

• Strawbery Banke Museum: Begin your visit with a trip to Strawbery Banke Museum, an outdoor history museum featuring restored houses, period gardens, and costumed interpreters. The museum provides a fascinating glimpse into over 300 years of New Hampshire history. Wandering through the historic homes and chatting with interpreters is like stepping back in time.
• Market Square: The heart of downtown Portsmouth, filled with boutique shops, cafes, and historic landmarks. It’s a great spot for a stroll and some shopping. I love the vibrant energy and variety of local artisans and boutiques here!
• Prescott Park: Relax at Prescott Park, a beautiful waterfront park known for its gardens, public art, and seasonal outdoor performances. In the summer, check out the Prescott Park Arts Festival for concerts and theater productions.
• Portsmouth Harbor Cruises: Take a scenic boat tour of Portsmouth Harbor. The cruises offer fantastic views of the coastline, historic forts, and lighthouses. It’s a great way to see the city from a different perspective.
• USS Albacore Museum: Explore this unique submarine museum, where you can tour the USS Albacore, a research submarine that once held the record for the world’s fastest submarine.

More Attractions to See in Portsmouth (If You Have Time)

• Isles of Shoals: Just off the coast, these small islands are perfect for a day trip. You can take a ferry from Portsmouth and enjoy a guided tour, beautiful views, and a bit of history.
• The Music Hall: Catch a show at this historic theater, which hosts a variety of performances, including concerts, films, and live theater.
• Seacoast Science Center: Located in Odiorne Point State Park, this interactive museum offers exhibits on marine life and the natural history of the New Hampshire coast. Great for families!

In summer, Prescott Park comes alive with beautiful flowers and outdoor performances. It’s also the best time for harbor cruises and visits to the Isles of Shoals.

Tip: Got more time? Consider a short drive to nearby attractions like Hampton Beach for a classic New England beach experience. However, it’s a bit honky tonk and not as nice as the beaches of Maine that you’ll find below.

Day 6: York and Ogunquit, Maine

As you cross the border into Maine, I highly recommend spending at least a day exploring the coastal towns of York and Ogunquit, some of the best places to visit in Maine. Just a 30-minute drive from Portsmouth, they offer stunning beaches, quaint villages, and scenic walks that capture the essence of Maine’s southern coast.

Start your day in York with a visit to the iconic Nubble Lighthouse. Perched on a rocky island just offshore, this picturesque lighthouse is one of the most photographed in New England. The views from Sohier Park are breathtaking, and the sight of the lighthouse against the Atlantic backdrop is simply stunning.

Also, spend some time at Long Sands Beach, a beautiful stretch of sandy shoreline perfect for a relaxing morning walk or a dip in the ocean. The beach is great for families, with gentle waves and plenty of space to spread out.

Then, head to Ogunquit, where my family has loved visiting regularly for generations. I recommend spending a night or two here, as it’s absolutely magical and there’s a ton to do.

Here are my favorite activities and attractions in Ogunquit

• Marginal Way: In Ogunquit, take a leisurely stroll along the Marginal Way, a scenic 1.25-mile coastal path that offers stunning ocean views and access to small beaches and rocky coves. The walk from Perkins Cove to Ogunquit Beach is one of my favorites, offering numerous spots to sit and soak in the scenery.
• Perkins Cove: Explore the charming Perkins Cove, a picturesque fishing village in Ogunquit. The area is filled with quaint shops, art galleries, and seafood restaurants. Don’t miss the opportunity to take a lobster boat tour with Bunny Clark Deep Sea Fishing or Finestkind Scenic Cruises.
• Trying to local food: For a memorable dining experience, head to The Lobster Shack at Perkins Cove. Enjoy fresh lobster rolls and seafood dishes while overlooking the scenic harbor. Another absolute gem is Barnacle Billy’s, which has stunning views of the cove!
• Ogunquit Beach: Spend the afternoon at Ogunquit Beach, known for its wide sandy shore and gentle surf. It’s a perfect spot for sunbathing, swimming, and beachcombing. The expansive beach and crystal-clear water make it an ideal place to relax and unwind.

After Ogunquit, I propose heading north to Portland, and saving Kennebunkport as a stop on the way back to Boston!

Days 7-8: Portland, Maine

Next up on this ultimate road trip from Boston to Maine is Portland, ME. Located about an hour north of Ogunquit, this coastal city is bursting with personality, from its lively arts scene to its historic charm and mouth-watering food. It’s the biggest city in Maine but still has that cozy, small-town vibe.

Portland truly has it all. From cobblestone streets and historic buildings to a bustling waterfront and fantastic food scene, there’s something here for everyone. I recommend spending at least 1 night here to really experience the energy and charm of the city.

Here are my top picks for having an awesome time in Portland:

• Old Port District: Start your visit by exploring the Old Port district, known for its cobblestone streets, 19th-century brick buildings, and vibrant shops and restaurants. Wander through the narrow streets, pop into unique boutiques, and grab a coffee at a local café. The Old Port’s charm and energy make it the heart of Portland. I love getting lost in the historic streets and discovering new treasures
• Portland’s Epic Food Scene: You have to try the lobster rolls at Eventide Oyster Co. Check out The Honey Paw and Duckfat – their food is incredible. And don’t forget to grab a pint at Shipyard Brewing Company! Looking to sample some local beers? Allagash Brewery is also a must.
• Portland Head Light: This iconic lighthouse is in Fort Williams Park and offers killer views of the rugged Atlantic coastline. It’s super photogenic, so have your camera ready!
• Eastern Promenade: Perfect for a chill walk or bike ride along the waterfront. You can also rent kayaks or hop on a ferry to explore nearby islands from here.
• Portland Museum of Art: If you’re into art, this place is a must-see. They’ve got an impressive collection of American, European, and contemporary pieces.
• Victoria Mansion: Also known as the Morse-Libby House, this beautifully preserved Victorian home gives you a peek into 19th-century life. The guided tours are really cool.

Additional Attractions in Portland

• Casco Bay Islands: Take a ferry and check out the Casco Bay Islands. Peaks Island is my favorite – it’s super quaint and you can easily rent bikes to explore. For ferry schedules, visit Casco Bay Lines.
• Maine Narrow Gauge Railroad Co. & Museum: You can ride historic narrow-gauge trains along the waterfront. Great for kids and train enthusiasts alike.
• Back Cove Trail: A 3.5-mile loop with fantastic views of the Portland skyline. Perfect for a morning jog or a relaxing walk.
• Deering Oaks Park: A beautiful park with walking trails, a pond, and a seasonal farmers’ market. Ideal for a picnic or just chilling out.

Portland is very walkable, so once you park, you can pretty much get everywhere on foot.

While spending time in Portland is amazing, there are several nearby towns and attractions that make for excellent day trips. Here are some places to check out if you have time.

Cape Elizabeth

• Fort Williams Park: Just a short drive from Portland, Fort Williams Park is home to the iconic Portland Head Light (mentioned above). The park itself is a great spot for picnics, hiking, and enjoying the stunning ocean views. The park’s expansive grounds and historical sites make it a fantastic place to explore for a few hours.
• Two Lights State Park: Located nearby, Two Lights State Park offers rocky headlands, picnic areas, and scenic ocean views. The park is named after the twin lighthouses at Cape Elizabeth, and it’s a perfect spot for a relaxing day by the sea. The rugged coastline and serene environment are worth the visit.

Freeport

• L.L. Bean Flagship Store: Freeport, just 20 minutes north of Portland, is famous for its outlet shopping, particularly the L.L. Bean Flagship Store, which is open 24/7. The store offers a wide range of outdoor gear and apparel, and the town itself is full of other great shopping opportunities.
• Wolfe’s Neck Woods State Park: For a touch of nature, visit Wolfe’s Neck Woods State Park in Freeport. The park features hiking trails, birdwatching, and beautiful views of Casco Bay. It’s a peaceful escape and perfect for a picnic or an easy hike. More information can be found at Wolfe’s Neck Woods State Park.
• Freeport Outlets: Besides L.L. Bean, Freeport is home to a variety of outlet stores where you can find great deals on clothing, accessories, and more. Some popular ones include Polo Ralph Lauren, American Eagle, J.Crew Factory, and Banana Republic Factory Store.

Sebago Lake

• Sebago Lake State Park: For those looking to enjoy freshwater activities, Sebago Lake State Park, about 45 minutes northwest of Portland, is an excellent choice.This is one of Maine’s largest and most popular lakes, offering swimming, boating, fishing, and hiking. Love that crystal clear water!
• Hiking Trails: The park has some easy hiking trails with stunning views of the lake and surrounding forest. One of my favorites is the Outer Loop from Cub Point, which is 3.5 miles.

Day 9: Must-See Stops Between Portland and Bar Harbor

• Brunswick: A historic town with a vibrant arts scene. Explore the diverse art collection at the Bowdoin College Museum of Art, and take some time to walk around the campus. Then, enjoy high-quality live performances at the Maine State Music Theatre.
• Bath: Known for its rich maritime history. Visit the Maine Maritime Museum for exhibits and shipyard tours, and take a guided tour of the historic Bath Iron Works shipbuilding facility.
• Wiscasset: A picturesque town famous for its lobster fishing, clam and worm digging, and seafood. Stop at Red’s Eats for one of the best lobster rolls in Maine, and tour the historic Castle Tucker with views of the Sheepscot River.
• Damariscotta: Known for its oyster farms and historic sites. Enjoy a boat tour with Damariscotta River Cruises to explore oyster farms and marine life, and visit the ancient Whaleback Shell Midden State Historic Site, which was formed by Native Americans over 1,000 years.
• Boothbay Harbor: A stunning seaside town. Wander through the Coastal Maine Botanical Gardens, New England’s largest botanical garden, and visit the historic Burnt Island Lighthouse, the second oldest surviving lighthouse in Maine.
• Rockland: A hub for art and maritime history. Discover American art, including works by Andrew Wyeth, at the Farnsworth Art Museum, and learn about Maine’s lighthouses at the Maine Lighthouse Museum.
• Camden: A picturesque harbor town. Hike to the top of Mount Battie in Camden Hills State Park for panoramic views, and enjoy the scenic waterfront and boat watching at Camden Harbor.
• Belfast: A charming coastal town with rich history. Take a stroll along the Belfast Harbor Walk and relax in the beautiful Belfast City Park with views of the harbor. Belfast City Park
• Blue Hill: Known for its scenic views and local charm. Hike to the summit of Blue Hill Mountain for stunning vistas, and stop by the Blue Hill Co-op for local foods, crafts, and a cozy café.

Taking the time to explore these towns will not only break up the drive from Portland to Bar Harbor, but will also give you a great taste of what coastal Maine looks like!

Days 10-12: Bar Harbor and Acadia National Park

Welcome to one of my absolute favorite places on the East Coast! As you reach the northern end of your Maine road trip, plan to spend 2-3 days in Acadia National Park and Bar Harbor. Acadia offers an abundance of natural beauty, while Bar Harbor provides a cozy base with excellent dining and lodging options.

For years, I’ve made the journey up to Acadia to see its rugged coastlines, serene lakes, and epic mountain views. It’s especially a cool destination to visit in the fall, when the coastal forests come alive with yellow, orange, and red leaves!

Whether you’re into hiking, biking, or just chilling with some incredible scenery, Acadia has you covered. Plus, it’s the oldest national park east of the Mississippi River.

Fun Things to See and Do in Acadia National Park:

• Cadillac Mountain: Drive or hike to the summit of Cadillac Mountain, the highest point on the East Coast. The views from the top, especially at sunrise, are insane. Sunrise is particularly magical and is one of the coolest experiences in Acadia.
• Jordan Pond Path: A scenic 3.3-mile loop around the clear waters of Jordan Pond. The crystal-clear waters with the Bubble Mountains in the background make this a perfect photo spot. Stop by the Jordan Pond House for their famous popovers with tea.
• Park Loop Road: A 27-mile road offering stunning views of the park’s forests, mountains, and coastline. Don’t miss pullovers like Thunder Hole, where waves crash into the rocks, creating a thunderous sound.
• Sand Beach: A beautiful beach nestled between mountains and rocky shores. Perfect for a relaxing break or a quick dip in the chilly Atlantic waters.
• Beehive Trail: A challenging but rewarding 1.4-mile hike with iron rungs and ladders leading to spectacular views. Not for the faint-hearted, but the view from the top is worth it.
• Bass Harbor Head Lighthouse: A picturesque lighthouse offering classic Maine coastal views. It’s especially beautiful at sunset.

More Epic Sights

• Thunder Hole: A natural rock inlet where the waves crash with a thunderous boom and splash. On particularly stormy days, the waves crashing into the rocks can send spray as high as 40 feet in the air. Best visited during high tide for the full effect – it’s a cool, dramatic sight!
• Carriage Roads: These 45 miles of car-free roads are perfect for biking or a leisurely walk. They were built by John D. Rockefeller Jr. and offer some of the best views in the park.
• Beehive Trail: Feeling adventurous? This hiking trail has iron rungs and ladders and offers a thrilling climb with amazing views at the top. Not for the faint of heart, though!
• Schoodic Peninsula: A quieter part of the park with stunning coastal views and fewer crowds. It’s a bit off the main path, but it’s worth the drive for some peace and quiet.

The Park Loop Road is a 27-mile scenic drive that takes you through some of the park’s most beautiful areas. It’s a great way to get an overview of Acadia and decide where you want to spend more time. If you’re new to hiking, start with easier trails like Ocean Path or Jordan Pond Path. For more experienced hikers, check out the Precipice Trail for a challenging adventure.

Staying in Bar Harbor, Maine

Wondering about the best hotels in Bar Harbor? I recommend staying in the Bar Harbor Inn (luxurious), Atlantic Oceanside Hotel (budget-friendly), or the Primrose Place (charming B&B).

Check out These Top Attractions in Bar Harbor:

• Shore Path: Start your day with a peaceful walk along the Shore Path, a scenic walkway that runs along the coast. It offers stunning views of Frenchman Bay and the Porcupine Islands.
• Village Green: The heart of downtown Bar Harbor, this picturesque park is perfect for a picnic or just relaxing. It’s also the hub for many local events and festivals.
• Bar Harbor Whale Watch Co.: Go on a whale-watching tour to see these magnificent creatures up close. They also offer puffin and lighthouse tours if you’re looking for more variety.
• Agamont Park: Located right by the harbor, this park offers beautiful views and is a great spot to watch the boats. Grab some ice cream from Ben & Bill’s Chocolate Emporium nearby and enjoy the scenery.
• Abbe Museum: Learn about the Wabanaki Nations and their history, culture, and art. It’s a fascinating museum and a great indoor activity if the weather isn’t cooperating.

Additional Attractions in Bar Harbor

• Bar Island: At low tide, you can walk across the sand bar from Bridge Street to Bar Island. It’s a fun adventure, but make sure to keep an eye on the tide schedule so you don’t get stranded.
• Wild Gardens of Acadia: Located 2 miles south of Bar Harbor, these gardens showcase native plants and are a lovely place to wander. They’re especially beautiful in spring and summer.
• Great Meadow Loop: A relatively easy hike that offers beautiful views and a chance to see some wildlife. It’s a great way to experience the natural beauty of the area without venturing too far from town.
• Atlantic Brewing Company: Take a tour of this local brewery and sample some of their craft beers. They also have a BBQ restaurant on-site that’s perfect for a laid-back lunch or dinner.
• Cottage Street: Explore the unique shops, galleries, and eateries on Cottage Street. It’s a great place to pick up souvenirs or enjoy a meal at one of the local restaurants.

Start your day early to enjoy a quiet walk along the Shore Path or through the downtown streets before they get busy with tourists. Rent a bike from Bar Harbor Bicycle Shop and explore the scenic carriage roads of Acadia National Park. It’s a fantastic way to see the park without a car.

Pro Tip: If you’re into stargazing, Acadia offers some of the darkest skies on the East Coast. Head to Sand Beach or Jordan Pond after dark for an incredible view of the night sky.

Alternative Itinerary Suggestion: Lubec, Maine

I highly recommend checking out West Quoddy Head Light, which offers breathtaking views of the rugged coastline and the Bay of Fundy. Quoddy Head State Park is also worth visiting with its hiking trails that lead to dramatic cliffs, bogs, and forests with panoramic ocean views. It’s a great spot for bird watching and enjoying the coastal scenery.

From there, you’re just across the border from Canada, where you can explore places in New Brunswick, Nova Scotia, and Prince Edward Island. Exploring Eastern Canada is a great way to continue your road trip…it truly gets wilder the further north you go!

Though if you want to continue exploring Maine, I have a few more recommendations below.

Days 13-14: Baxter State Park, Maine

Ready to see my all-time favorite destination in Maine? I saved the best for last! After exploring the stunning landscapes of Acadia National Park, head inland to the majestic wilderness of Baxter State Park. This is the perfect place to spend your final days of your Maine road trip.

Located about 3.5 hours northwest of Bar Harbor, Baxter State Park is a sprawling, rugged area. It’s known for its pristine beauty, extensive hiking trails, and Maine’s highest peak, Mount Katahdin.

Baxter State Park offers a completely different experience from the coastal beauty of Acadia. Here, you’ll find towering mountains, deep forests, and serene lakes. I love going camping and hiking here, especially during the fall!

I recommend staying in Baxter for at least 2-3 days. This will give you enough time to take it slow and do at least one longer hike. Plan to stay in Millinocket, which is right outside of the park. Here’s what I recommend doing.

Coolest Attractions and Activities in Baxter State Park

• Mount Katahdin: The crown jewel of Baxter State Park, Mount Katahdin is Maine’s highest peak at 5,267 feet. Hike the iconic Knife Edge Trail for an exhilarating and challenging trek with breathtaking views. This trail is not for the faint-hearted but offers an unforgettable experience that reminds me of Angel’s Landing in Utah. It’s the northern terminus of the Appalachian Trail, which spans over 2,000 miles from Georgia to Maine.
• Chimney Pond: For those seeking a less strenuous hike, the trail to Chimney Pond offers stunning views of Katahdin and its surrounding peaks. The 3.3-mile trail leads to a beautiful glacial cirque and is a popular spot for day hikes and backcountry camping.
• Daicey Pond and Kidney Pond: These serene ponds offer excellent opportunities for canoeing, kayaking, and fishing. Canoes and kayaks are available for rent, and the calm waters make for a peaceful paddle surrounded by wilderness.
• South Branch Pond: Located in the northern section of the park, South Branch Pond is another great spot for water activities and offers several hiking trails with varying difficulty levels. The area’s beauty and tranquility make it a perfect retreat.
• North Traveler Mountain: For a less crowded hike with rewarding views, try the North Traveler Mountain Trail. It’s a challenging hike but offers stunning vistas of the park’s northern regions.

Quick tip: Baxter State Park has a strict quota system for hiking Mount Katahdin. Make sure to secure your permits and campground reservations well in advance, especially during the peak season.

Baxter State Park offers an incredible end to your Maine road trip, with its wild beauty and outdoor adventures. Whether you’re summiting Katahdin or enjoying the peaceful ponds, these final days truly showcase Maine’s diverse landscapes.

On the way back to Boston, I will recommend some cool stops along the way if you have time!

Routes and Tips for the Ride Back to Boston

I-95 South via Bangor and Augusta

Inland Route via Moosehead Lake and Rangeley Lake

Mountain Route via Sugarloaf and the White Mountains

• Mountain Scenery: Drive through the western part of Maine to experience the majestic Sugarloaf Mountain area. Depending on the season, you can enjoy skiing, hiking, or simply the mountain views.
• White Mountains: Continue into New Hampshire’s White Mountains, stopping at places like Franconia Notch State Park or the Kancamagus Highway for some of New England’s most beautiful mountain scenery. This route takes about 8-9 hours with stops.

Route 1 South via Coastal Maine

If You Have Time: Spend a Day in Kennebunkport, Maine

This is another perfect place to wrap up your road trip! This charming coastal town in Maine is known for its beautiful beaches, historic sites, and fantastic seafood. It’s also famous for being a summer retreat for former President George H.W. Bush and his family. Kennebunkport offers a blend of relaxation and exploration, making it a great spot to unwind after your adventures.

Add these attractions to your Maine itinerary:

• Dock Square: The heart of Kennebunkport, filled with boutique shops, art galleries, and great restaurants. It’s the perfect place to wander, shop, and grab a bite to eat. Don’t miss the local clam chowder!
• Walker’s Point: Drive by this famous summer home of the Bush family. There’s a scenic overlook where you can stop and take photos of the stunning ocean views and the Bush estate.
• Gooch’s Beach: A long, sandy beach that’s perfect for a relaxing day by the ocean. It’s great for swimming, sunbathing, and beachcombing. The parking can be a bit tight, so arrive early.
• Cape Porpoise: A quaint fishing village just a short drive from downtown Kennebunkport. Check out the working lobster pier and grab some fresh seafood at Cape Porpoise Chowder House. The views of Goat Island Lighthouse are stunning.
• St. Ann’s Episcopal Church: This historic stone church is beautifully situated on the coast with amazing views. The grounds are open to the public, and it’s a peaceful spot to visit.

More Spots to Visit

Things to Consider When Planning Your Road Trip

Where to Start Your Road Trip

The best place to kick off your Boston to Maine road trip is right in the heart of Boston. As the capital city of Massachusetts, Boston is brimming with history, culture, and iconic landmarks. Start your adventure by exploring the Freedom Trail, strolling through the Boston Common, and indulging in some delicious food at Quincy Market.

Plus, Boston is well-connected with major highways like I-95, making it the perfect starting point for your journey up the coast. Once you’ve soaked in all the city has to offer, hit the road and let the adventure begin!

Best Time of Year for a Boston to Maine Road Trip

Number of Days for a Boston to Maine Road Trip

Other Destinations to Consider on Your New England Road Trip

• Freeport, ME: Home to the famous L.L. Bean flagship store, this quaint town is a shopper’s paradise. Don’t miss the beautiful Wolfe’s Neck Woods State Park nearby.
• Camden, ME: Known for its picturesque harbor and charming downtown area, Camden is a great spot to enjoy sailing, hiking, and stunning views from Mount Battie.
• Newburyport, MA: A delightful coastal town with a rich maritime history, scenic waterfront, and fantastic dining options. It’s also a great place for whale-watching tours.
• Rockland, ME: Famous for its annual Lobster Festival and the Farnsworth Art Museum, Rockland is a cultural hub with a lively arts scene and beautiful coastal views.
• Concord, MA: Step into history with a visit to this town known for its Revolutionary War sites, literary history, and beautiful Walden Pond.
• North Conway, NH: Nestled in the White Mountains, this town is perfect for outdoor enthusiasts. Enjoy hiking, skiing, and stunning mountain views. The nearby Kancamagus Highway is a must-drive for fall foliage.
• Mystic, CT: Famous for its maritime history and the Mystic Seaport Museum, this charming town offers a mix of history, beautiful scenery, and a fantastic aquarium.

FAQs About the Boston to Maine Road Trip

What does a 5-day road trip from Boston to Maine look like?

What is the best route to take from Boston to Maine?

How long does it take to drive from Boston to Maine?

The direct drive from Boston to Kennebunkport, ME, takes about 1.5 to 2 hours without stops. However, to fully enjoy the sights and make the most of your New England road trip, plan for several days.

Can you take a road trip from Boston to Maine in 7 days?

Absolutely! Here’s a sample 7-day itinerary:

• Day 1: Boston, MA: Explore the historic and cultural sites like the Freedom Trail and Quincy Market.
• Day 2: Salem, MA: Visit the Salem Witch Museum, House of the Seven Gables, and the waterfront.
• Day 3: Portsmouth, NH: Enjoy the historic downtown, Prescott Park, and waterfront.
• Day 4: Kennebunkport, ME: Relax at Gooch’s Beach, explore Dock Square, and drive along Ocean Avenue.
• Day 5: Portland, ME: Discover the Old Port District, Portland Head Light, and local seafood spots.
• Day 6: Bar Harbor, ME: Experience Acadia National Park and explore the charming town of Bar Harbor.
• Day 7: Return to Boston: Take a scenic drive back with stops along the way.

What kind of car is best for this trip?

Are there any tolls on the way?

Yes, there are tolls on I-95, especially as you enter and leave major cities like Boston and Portland. Make sure to have cash or an E-ZPass for smoother travel.

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