Boston to Maine Road Trip

Boston is the ideal spot to start this coastal New England road trip. Get an early start and enjoy a coffee as you stroll through the city's historic Italian North End neighborhood. Sit down for a morning bite at Theo's Cozy Corner Restaurant or Anthony's Café on the Waterfront before exploring a few of Boston's highlights.

To experience over a dozen of the city's key attractions in a short period of time, set out on foot and follow the Freedom Trail. This well-marked walking route includes North End sites like Copp's Hill Burying Ground, the Old North Church, and the Paul Revere House before tracing a path through the heart of Boston. As you follow the path, you can explore historic Faneuil Hall where patriots met to plan the Revolution. Here you can also visit the Old State House and explore the Granary Burying Ground. Finish with a quick tour of the Boston Common before heading north.

After leaving Boston, follow Interstates 93 and 95 to Portsmouth, one of New Hampshire's most engaging seaside towns. This waterfront setting has served as a key Atlantic Ocean port for centuries. It is filled with majestic mansions and modest homes, many of which date back to the 18th century.

If history piques your interest, make your way to the Strawbery Banke Museum. It is filled with exhibits that explore the cultural history and everyday life of Portsmouth from the 17th to 19th centuries. If art is your affinity, peruse the downtown galleries or check out the latest display at the Portsmouth Music and Arts Center.

Next, get back on Interstate 95 and head north to Kennebunkport, which is just over the Maine border. One could easily spend a leisurely week here browsing the boutiques and relaxing on the beach, you can still see the best of Kennebunkport in a brief visit.

First, make your way to Dock Square, located in the center of town. Here you can pick up a few souvenirs, view ocean-inspired artwork in the many galleries, and lounge on a sunny patio. After a cup of coffee and a bite to eat at Dock Square Coffee House, head to town-favorite Gooch's Beach and enjoy the sea breeze.

After another 40 minutes on Interstate 95, you'll arrive in Portland, Maine's biggest and most vibrant city. Park in Old Port and spend an hour or two getting lost among the 19th-century warehouses, unique shops, and intriguing museums that line Congress Street. Treat yourself to the raw bar at Eventide Oyster Co. and explore the neighboring Arts District, home to the Museum of African Culture and the Portland Museum of Art.

Before getting back in the car, make a quick stop at the Eastern Promenade, one of Portland's most scenic areas. Located just north of Old Port, the Eastern Promenade stretches for about two miles along the waterfront, offering lovely views of the sea and plenty of space to get some exercise on the walking trails. If you want to do a little sunbathing or swimming, head to East End Beach, the only public beach in Portland.

When you're ready to hit the road again, take scenic U.S. Highway 1. You'll get frequent glimpses of the sea and have great opportunities to pull over and experience life along this wild coast.

When you pull into Bar Harbor, you'll be enchanted by this small seaside town. Here you can watch sailboats in the waterfront and then stop by West Street to marvel at some of the mansions.

Next, head to the town's main drag, a buzzing strip where you'll find countless boutiques, souvenir shops, and ice cream stands stretching several blocks inland from the Mount Desert Narrows. If you love seafood, you'll easily find a dozen or more lobster shacks and fish houses to choose from. Indulge in clam chowder at Geddy's or enjoy lobster and oysters at the Fish House Grill.

You'll want to get up early to catch a sunrise from Cadillac Mountain in neighboring Acadia National Park. Spend the morning or the entire day hiking, biking, or swimming in this beautiful national park. If you visit during the summer, sign up for an unforgettable ranger-guided bike tour or a cruise through Frenchman Bay.

After a gorgeous day in Acadia National Park and a leisurely meal in Bar Harbor, you'll want to stay in town for at least another evening. Hop back in your rental car and explore even more of Bar Harbor and coastal Maine the next day.