Boston to Maine Road Trip Guide
Leave behind the bustle of Boston for fresh air and the open road. A northbound road trip from Massachusetts into Maine weaves together historic harbor towns, dense woodlands and dramatic shorelines. Cross the Piscataqua River Bridge on and the famous border sign welcomes you to Vacationland, where you’ll enjoy a glimpse of “The Way Life Should Be.” Feel the shift as city traffic fades into quieter roads and coastal stretches. This town-by-town guide maps out the mileage and must-do experiences to help you make the most of your trip.
Boston to Maine Road Trip: Must-Visit Towns
Chattery
Distance from Boston to York: ~58 miles (1 hour)
Top Things to Do: Stop at the Maine State Visitor Information Center for maps and other helpful trip information, then continue to Fort McClary, a historic fort with nature trails and views of the Piscataqua River.
York
Distance from Boston to York: ~65 miles (1 hour 15 minutes)
Top Things to Do: Just off the U.S. Route 1 in York, browse the York Village shops and discover a treasure trove of gifts at Bell Farm Shops, where curated finds range from birdhouses and whimsical garden decor to art books and small-batch beauty products. Then head for the coast, where the 19th-century Nubble Lighthouse rises from a rocky island just offshore—one of Maine’s most photographed seaside views.
Ogunquit
Distance from Boston to Ogunquit: ~75 miles (1 hour 30 minutes)
Top Things to Do: Ogunquit, meaning beautiful place by the sea, lives up to its name, with a welcoming atmosphere, thriving arts and an oceanfront shaped by the elements. Visit the Ogunquit Museum of American Art to see modern and contemporary works, then stroll the iconic Marginal Way, a 1.25-mile paved cliffside path that overlooks the Atlantic Ocean and showcases the state’s coast at its most wild. At the end of the path, set out to explore Perkins Cove, a working fishing village where you can cross a historic pedestrian drawbridge to watch lobster boats bring in the day’s catch or pop in and out of independently owned shops and restaurants.
Kennebunk & Kennebunkport
Distance from Boston to Kennebunk and Kennebunkport: ~85 miles (1 hour 45 minutes)
Top Things to Do: Discover the quaint, riverside charm that welcomes you upon arriving in Kennebunk and neighboring Kennebunkport. After your drive, visit the Seashore Trolley Museum to explore its collection of historic streetcars, then stretch your legs at Goose Rocks Beach, a family-friendly spot or find your sea legs with a guided kayak or stand-up paddleboarding tour. Stroll through Dock Square, the heart of the town, and browse local boutiques while hunting for lobster-themed souvenirs or an iconic Maine lobster roll.
Portland
Distance from Boston to Portland: ~110 miles (2 hours)
Top Things to Do: Maine’s largest city, Portland, becomes a must-stop if you’re foodie or are seeking out museums and galleries. This cultural and culinary capital along Casco Bay blends acclaimed seafood restaurants and picturesque lighthouses well worth a trip. Start with the Portland Museum of Art to get a glimpse into Maine’s thriving arts scene, then head to nearby Fort Williams Park on Cape Elizabeth to marvel at Portland Head Light. In town, trade Boston’s historical bricks for the cobblestone and brick-lined streets of the Old Port district. Sample everything from oysters to clam chowder or an award-winning craft beer before taking a scenic ferry ride across Casco Bay to the nearby islands.
Rockland & Camden
Distance from Boston to Rockland and Camden: ~185 miles (3 hours 30 minutes)
Top Things to Do: Driving up the Midcoast brings you to Penobscot Bay, where the mountains meet the sea. In Rockland, a Main Street Community, explore the art scene at the Farnsworth Art Museum and Center for Maine Contemporary Art before taking the almost-mile walk out to the Rockland Breakwater Lighthouse, which stands out as the centerpiece of the Rockland Harbor. Just a short drive north in Camden, hike or drive to the top of Mount Battie in Camden Hills State Park for panoramic harbor views. For an entirely new perspective, swap your car for a boat and set sail on a historic Windjammer for a sunset cruise right out of the harbor.
Bangor
Distance from Boston to Bangor: ~235 miles (3 hours 45 minutes)
Top Things to Do: Heading inland, experience riverfront history in Bangor. Known as the booming lumber capital and the birthplace of Paul Bunyan, you can visit and snap a photo of the 31-foot-tall Paul Bunyan statue, built for the city’s 125th anniversary celebration. If you’re a pop-culture enthusiast, drive past author Stephen King’s former home and draw inspiration from its wrought-iron bat and spiderweb gate or from the town itself which inspired the fictional town of Derry. For a change of scenery, bike or walk the Bangor Waterfront Trail for views of the Penobscot River, then get out on the water with a boating excursion. In downtown Bangor, enjoy live music during the Waterfront Concert Series. For a quieter escape, retreat into the Bangor City Forest for shaded pine trails.
Bar Harbor
Distance from Boston to Bar Harbor: ~280 miles (4 hours 45 minutes)
Top Things to Do: Embark on the ultimate Maine road trip to Bar Harbor, the gateway to Acadia National Park. Along the way, stop in Ellsworth, a Main Street Community full of locally-owned shops before continuing your trip. Before crossing onto Mount Desert Island, stop at the Acadia Gateway Center, where you can leave the car behind and hop aboard the Island Explorer for a stress-free way to explore Acadia and discover the quieter side of the island. Or, continue by car across the Trenton Bridge on Route 3 East. Cruise the scenic Park Loop Road, hike the Ocean Path or catch the sunrise from the highest point on the eastern seaboard atop Cadillac Mountain. Back downtown, walk along Shore Path before pulling up a chair to enjoy a traditional Maine lobster bake right along the water, offering a peaceful contrast from typical city life.
Toll Payment along the Maine Turnpike
You will encounter tolls along the Maine Turnpike on I-95 during your road trip. Unlike some states, Maine is not a “Pay-by-Plate” system, so it’s best to be prepared before you travel. Drivers can pay tolls with an E-ZPass or cash.
The E-ZPass is compatible with more than 40 highways, bridges and tunnels throughout the eastern United States. Toll costs vary depending on your route but most travelers can expect to pay only a few dollars along portions of the Maine Turnpike. Before you hit the road, use the Maine Turnpike Authority’s toll calculator to estimate your trip costs.