Quaint New England Towns | A Drive Through Autumn Landscapes

Days 1-2

Boston

Fly into Boston, where you will be met and transferred to your hotel where you will spend two nights.

Although many people know about Boston’s rich history and its role in the Revolutionary War, they may not be aware of the city’s world-class museums, numerous universities and abundant shopping opportunities. Begin your exploration of the city on The Freedom Trail with its 16 historic stops, including the famous Old North Church and the Paul Revere House. Spend an afternoon (or a day) enjoying the Museum of Fine Arts’ extensive collection or the eye-opening exhibits at the Museum of Science. For a more intimate experience, visit the Isabella Stewart Gardner Museum or the Nichols House Museum. Walk across the Charles River on the Longfellow Bridge or take the “T” (underground) to Cambridge to explore the ivy-trimmed campus of Harvard University and nearby cafés and bookshops. Shoppers will enjoy areas such as Newbury Street in the Back Bay (high-end boutiques in restored brownstone houses), Copley Place (a two-level mall with top brand-name stores) and the famous Faneuil Hall Marketplace (100-plus shops and pushcarts as well as 50 restaurants, pubs and food vendors). Sports fans should plan to watch a Boston Red Sox baseball game (April through October) and take a tour of Fenway Park, the oldest Major League Baseball Park in the country. If the weather is nice, stroll through the Boston Common and take a ride on one of the famous Swan Boats in the Public Garden.

As you can see, there is a lot to explore in Boston, so if you would like to add an extra day, please let us know.

2 nights Boston, Massachusetts    

Days 3-4

Boston to Kennebunkport

Collect your car this morning and head north along the scenic New England coast through Massachusetts. Infamous for the Salem Witch Trials of 1692, Salem is a colourful city with a rich maritime heritage, Victorian architecture and fascinating stories that span nearly 400 years. Continue through Manchester-By-The-Sea, Massachusetts made famous by the award-winning 2016 movie of the same name) and historic Rockport, Massachusetts, an inspiration to painters since legendary American painter Winslow Homer spent two summers in this area (1873 and 1880). After exploring charming Rockport, head to Portsmouth, New Hampshire. Settled in 1623, Portsmouth’s historic past and cultural strengths make it an attractive destination. It’s also a gateway to New Castle, one of New Hampshire’s smallest towns and home of the Fort Constitution Historic Site. After exploring the fort, depart for Maine, where your first stop is Ogunquit, named by the Abenaki tribe, meaning ‘beautiful place by the sea’. Enjoy the vintage feel of this charming place, stroll among quaint buildings or explore the Marginal Way ocean path. The final stop today is Kennebunkport, Maine, located along the Atlantic Ocean and Kennebunk River. Settled in the 1600s and a long-time ship building centre, the city’s resident sea captains built fine mansions here; some of these original homes are now lovely inns. Enjoy its shops and restaurants or taking a walking tour to learn its history.

2 nights Kennebunkport, Maine    

Day 5

Kennebunkport to Camden

Today’s first stop is Old Orchard Beach. Here, you can enjoy seven miles of sandy beach and Old Orchard Beach Pier, stretching more than 500 feet over the Atlantic Ocean. Continue north to the historic seacoast city of Portland with its funky galleries, one-of-a-kind shops, diverse restaurants and many lighthouses (six within 30 minutes’ drive of the city – among them, Portland Head Light, one of the most photographed in the USA). Here, take the time to explore the Arts District and Old Port historic district. As you continue through the mid-coast region of Maine, past quaint New England cottages and quiet coves, be sure to stop at Pemaquid Point Lighthouse in Bristol. The lighthouse itself is beautiful and the unusual rock formations bordering the structure make this a fabulous photo spot as well. Rockland, known as the ‘Gateway to Penobscot Bay’, is a classic working harbour town and home to galleries, craft shops, fine dining and the Maine Lighthouse Museum with its fine collection. The final stop today is in Camden, where locals say ‘ the mountains meet the sea’. A culinary mecca, Camden features charming little streets, huge schooners and locally owned art galleries, making it the perfect destination to overnight.

1 night Camden, Maine

Days 6-7

Camden to Bar Harbor & Acadia National Park

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.

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 metres) is the highest peak on the U.S. Atlantic Coast.

2 nights Bar Harbor, Maine             

Day 8

Bar Harbor & Acadia National Park to Bethel

Travel east to Bethel, a charming town nestled amidst the picturesque mountains and lakes of western Maine. Known for its stunning natural beauty, vibrant outdoor activities, and quaint downtown, Bethel offers a quintessential New England experience.

1 night Bethel, Maine 

Day 9

Bethel to North Conway

Take a full day to explore the White Mountains of New Hampshire. First, travel to Gorham and join Highway 15 (Three Rivers Scenic Drive) which will take you past Mount Washington and the mountain pass known as Pinkham Notch. (We recommend that you stop to take the cog railway or drive to the summit of Mount Washington – known as ‘the home of the world’s worst weather’. Here, you can visit the weather station and Extreme Mount Washington museum.) Outdoors lovers won’t want to miss Pinkham Notch, a stunning natural landmark created by glaciers, erosion and rivers, and separating three mountain ranges. Take the opportunity to hike trails that accommodate all skill levels or relax on a Gondola ride and enjoy the views in Wildcat Mountain Ski Area. The journey ends in North Conway in the heart of Mt. Washington Valley, home to nearly 100 shops, outlet stores, fine art galleries, locally made crafts, restaurants, pubs and live entertainment.

1 night North Conway, New Hampshire   

Days 10-11

North Conway to Manchester

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 Manchester at the gateway to the Green Mountains.

Explore Vermont’s Green Mountains National Forest, beautiful in all seasons. Autumn is the most colourful time of year here, due to the brilliance of the changing foliage, but this area has something for outdoor enthusiasts year-round. Enjoy pastoral views as you travel along Route 7a through Manchester and Bennington, Vermont, where you should stop to photograph the unusual covered bridges.

2 nights Manchester

Day 12

Manchester to Stockbridge

Visit Mass MoCA in North Adams, Massachusetts before continuing to Stockbridge, home to the Norman Rockwell Museum, well worth a visit for its extensive collection of the beloved American illustrator’s original works.

1 night Stockbridge, Massachusetts          

Day 13

Stockbridge to Mystic

From Stockbridge, travel south to the Connecticut coast and Westport. The waterfront has a row of attractive red brick buildings, and the area enjoys some of the prettiest scenery in the state, making this a good stop for a picnic or a stroll through town. Further along the coast, stop at Old Saybrook, famous for being the home of Katharine Hepburn (and now hosts The Katharine Hepburn Cultural Arts Center). Filled with impressive architecture and many remarkable buildings (including historic manor houses and the Saybrook Breakwater Lighthouse), this is a perfect stop for lunch. Continue to Mystic, an attractive seaside village with a rich heritage. Originally one of the area’s most important seaports, its history has been preserved at the Mystic Seaport, one of the country’s largest maritime museums. Visit Main Street, many delicious seafood restaurants, quaint shops and the famous Mystic Pizza restaurant, made famous in the 1988 movie.

1 night Mystic, Connecticut         

Days 14-15

Mystic to Cape Cod & The Islands

Take Highway 1 to Narragansett, Rhode Island, known for its sandy beaches, and then take Highway 1a along the coast and across the Jamestown Bridge to Newport, one of the USA’s original playgrounds for the rich and famous. Newport retains a luxurious charm and many of its Gilded Age mansions are open to the public for tours. If you are tennis fan, also check out the International Tennis Hall of Fame in Newport. Next, drive to charming Cape Cod, where your day’s journey ends.

If you have time, we would strongly recommend a night or two in Rhode Island so that you can visit the mansions and enjoy the town.

The beach towns of Cape Cod could easily entertain visitors for several weeks or more. Talk to your travel consultant to discuss what community best suits your style, from the bustle and fun of Falmouth on the Lower Cape to the flower-adorned cottages of Orleans and the dune-swept beaches of Eastham and Truro on the Outer Cape. If you are not happy staying in Chatham, please let us know which village you would prefer. Busy Provincetown, an LGBT-friendly city at the tip of the Outer Cape, offers eclectic shops, galleries and restaurants, as well as natural beaches and stellar whale watching. The Cape’s scenic out islands – Martha’s Vineyard and Nantucket – can be reached via ferry or small plane.  Summer is high season on Cape Cod which means that accommodation fills up quickly: the shoulder seasons of spring and autumn offer a more peaceful stay.

2 nights Cape Cod

Day 16

Cape Cod & The Islands

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 Patuxet  is a must-visit – a fascinating, interactive view of the life of the early American colonists in a harsh land.  From there, return your car to the airport in time for your onward or homeward flight.