13-Day Quaint New England Towns

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Travel north along the scenic New England coast, stopping in Salem, known for the 1692 witch trials and maritime history. Pass through picturesque towns like Manchester-by-the-Sea and Rockport, a favorite of artists. Continue to Portsmouth, New Hampshire, and visit the historic Fort Constitution in New Castle. Then head to Ogunquit, Maine, a charming seaside town with the Marginal Way coastal path, before ending the day in Kennebunkport, known for its seafaring heritage and historic homes.

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Depart Kennebunkport and head north along Maine’s scenic coast. Stop at Old Orchard Beach to enjoy its sandy shoreline and ocean pier. Continue to Portland, a lively seaport city known for its lighthouses, Old Port historic district, and art scene. On the way up the mid-coast, stop at Pemaquid Point Lighthouse in Bristol for spectacular ocean views and photo opportunities. Pass through Rockland, home to the Maine Lighthouse Museum and a classic harbor vibe, before reaching Camden, a charming town where the mountains meet the sea. Spend the night in Belfast, ME.

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Follow the scenic shoreline of Penobscot Bay to Lincolnville in the heart of the Maine coast. This off-the-beaten-path place is a perfect spot to enjoy breathtaking views of the bay. Next, visit the picturesque town of Blue Hill to enjoy a laid-back and charming getaway. In addition to its historical architecture and shipbuilding roots, Blue Hill is also a gateway to Acadia National Park. Today’s final stop is Bar Harbor on Mount Desert Island, featuring elegant Victorian architecture, and situated between the blue waters of Frenchman Bay and the woodlands of Acadia National Park.

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Before travelling inland, take the morning to explore Acadia National Park, known for its rugged beauty. Expect to see glorious mountains and abundant wildlife and hear the thunder of crashing waves. Steep slopes rise above the rocky shore, including Cadillac Mountain, which at 1,529 feet (465 meters) is the highest peak on the U.S. Atlantic Coast. Travel east to Bethel, one of Maine’s popular mountain villages, and a hub of outdoor activities from skiing in winter to hiking and biking in summer. The walkable city center has everything visitors need. Stay the night in Gorham.

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Spend the day exploring New Hampshire’s White Mountains. Travel via the scenic Three Rivers Drive past Mount Washington and Pinkham Notch, with optional stops at the summit, weather station, or Extreme Mount Washington museum. Enjoy hiking or a relaxing gondola ride in Wildcat Mountain Ski Area. End the day in North Conway, a lively mountain town with shops, galleries, and entertainment.

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From North Conway, explore more of the White Mountains, taking the scenic Kancamagus Highway, and planning a photo op at Albany Covered Bridge along the way. Next, stop at Flume Bridge, a covered bridge open to cars, on your way to spectacular Franconia Notch State Park with its many trails, aerial tramway, wildlife watching and other recreational activities. Journey through Hanover, New Hampshire, home to Dartmouth College, and on to Woodstock, Vermont, which is full of quintessential New England charm, with a village green, covered bridge and historic architecture. Continue to the Rutland area in the Green Mountains for a two-night stay.

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Today, explore Vermont’s Green Mountains National Forest, beautiful in all seasons. Autumn is the most colorful time of year here, due to the brilliance of the changing foliage, but this area has something for outdoor enthusiasts year-round. A nice town to visit today is Manchester, in the heart of the Green Mountains.

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Enjoy pastoral views as you travel along Route 7a through Manchester and Bennington, Vermont, where you should stop to photograph the beautiful covered bridges before arriving in North Adams, Massachusetts for lunch. Here, you enter the Berkshires, a rural region in the mountains of western Massachusetts dotted with villages and towns. Continue to Stockbridge, home to the Norman Rockwell Museum, well worth a visit for its extensive collection of the beloved American illustrator’s original works. Overnight in the nearby town of Lenox

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Travel from Lenox to the scenic Connecticut coast, stopping first in Westport to enjoy its charming waterfront and red-brick buildings—ideal for a picnic or a stroll. Continue to Old Saybrook, known for its historic architecture and as the home of Katharine Hepburn. It’s a great place to stop for lunch and visit the Katharine Hepburn Cultural Arts Center. End the day in Mystic, a historic seaside village famous for its maritime heritage, Mystic Seaport Museum, quaint shops, seafood restaurants, and the iconic Mystic Pizza.

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Travel along the scenic coast from Mystic to Newport, Rhode Island, passing through Narragansett, known for its sandy beaches. In Newport, explore elegant Gilded Age mansions or visit the International Tennis Hall of Fame. Then continue to Cape Cod, where charming beach towns await. From lively Falmouth to artsy Provincetown, the Cape offers something for every traveler. Optional ferry trips to Martha’s Vineyard and Nantucket add to the experience. Summer is peak season, while spring and fall bring a more relaxed atmosphere.

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After your visit to Cape Cod, drive to Plymouth, ‘America’s hometown’, where the Pilgrims landed in 1620 in search of a home and religious freedom. Plimoth Plantation is a must-visit – a fascinating, interactive view of the life of the early American colonists in a harsh land. Depart Plymouth and continue to Boston, where your journey will end.