New England Road Trip: World-Class Culture and Fresh-Air Adventures

Take a cruise along this scenic loop that’s filled with urban attractions, rugged coasts and gorgeous mountains. Start in Boston, a friendly cosmopolitan center and the largest city in Massachusetts, before venturing into the three adjacent states of Maine, New Hampshire and Vermont. Along the way, stop to stroll through quaint villages, tour fascinating historic sites and soak up the natural beauty of the region.

Boston, Massachusetts: Gateway City Loaded with Heritage

Fly into Boston Logan International Airport (BOS), the primary gateway to New England and Massachusetts, and rent a car. You may want to park it at your hotel for this first road trip stop and get around Boston the way the locals do – on foot, using rideshares and taking public transportation. Begin by exploring Boston Public Garden and Boston Common, two neighboring parks at the city’s heart. For a truly iconic outing, take a ride in a Swan Boat on the pond in the Public Garden – they’ve been running since 1877. Delve further into Boston’s rich history along the Freedom Trail, a 4-kilometer walking route encompassing 16 significant historic sites. Of the scores of museums in the city, most are well worth a visit, including the stately Museum of Fine Arts, the fascinating Museum of Science and the Nichols House Museum – a grand 1804 residence in the uber-quaint Beacon Hill neighborhood, complete with period furnishings. Go shopping on high-end Newbury Street in the Back Bay neighborhood and check out the merchants and food carts in Faneuil Hall Marketplace and Quincy Market. Tour historic Fenway Park, home of the Boston Red Sox and the oldest Major League Baseball park in the USA, then hit the road and head north.

Portsmouth, New Hampshire: 400 Years of History on the Riverfront

Drive about an hour north from Boston to reach picturesque Portsmouth, New Hampshire, overflowing with charm from its perch on the Piscataqua River. Market Square, the traditional center of this port city, has architecture dating back to the 1700s. Join a walking tour of historic homes, the working waterfront and Prescott Park. The park is an oasis on the river, featuring extensive flower beds and playing host to the Prescott Park Arts Festival, one of New England’s most popular summer festivals. The nearby Strawbery Banke Museum brings the area’s heritage to life in 37 historic homes surrounded by period gardens and populated by costumed docents. Islands just off the coast offer accessible adventure and rugged beauty. Drive to Peirce Island and wander along walking paths sprinkled with historic markers, enjoy a picnic with water views and launch a kayak from the boat ramp. New Castle Island can also be reached by car – climb the Portsmouth Harbor Lighthouse, tour the colonial Fort Constitution Historic Site and picnic in the sea air at Great Island Common. Take a boat cruise to the Isles of Shoals, a group of sparsely populated islands. When you’re ready to move on, drive across the state line into Maine, stopping to stretch your legs in Portland or Camden on the way to the next stop, Bar Harbor.

Bar Harbor, Maine: Charming Coastal Town and Spectacular Park

Wind your way up the rocky Maine coast – taking a break to climb lighthouses and admire the views – until you reach Mount Desert Island, home to Bar Harbor and Acadia National Park. Stroll around the walkable downtown, which overlooks Frenchman Bay, and shop for Maine-made goods including watercolor paintings of picturesque harbors, lobster boats and tall ships. Wander down West Street and spot elegant Victorian architecture – the former summer homes of wealthy 19th-century families. Ready for an outdoor adventure? Head just outside town to Acadia National Park, where you can hike to the top of Cadillac Mountain, the highest peak on the Atlantic Coast; kayak around the craggy shoreline; or drive the Park Loop Road, pausing to watch the waves crashing at Thunder Hole and take photos of the Cranberry Isles. For a quintessential Maine experience, take a cruise on the Lulu, a traditional Downeast-style lobster boat, to get a first-hand look at lobster fishing, watch for seals and enjoy postcard-worthy sights. Sample fresh lobster in waterfront restaurants back in Bar Harbor. In the morning, drive west into the mountains to reach the village of Bethel.

Bethel, Maine: Quaint Village Amid Outdoor Adventures

Set among western Maine’s lakes and mountains, Bethel is a quaint village with a downtown full of shops, restaurants and bed-and-breakfast inns. The Sunday River Resort offers four seasons of fun, from skiing and snowshoeing in winter to hiking, biking, ziplining and golf in summer. At Bethel Outdoor Adventure Campground & River Trips, set on the banks of the Androscoggin River, visitors can rent canoes, kayaks, tubes or paddleboards and go paddling among the Mahoosuc Mountains. Other outdoor fun includes searching for precious gems and minerals, and walking across the Burma pedestrian suspension bridge to Hastings Island, where you can follow a trail to see birds and wildlife. Drive 20 minutes from Bethel to Grafton Notch State Park and hike through spectacular gorges to peaks and waterfalls. The park is home to a portion of the Appalachian Trail, so watch for through-hikers heading north to the trail’s end at Mount Katahdin. The area around Bethel is nothing if not scenic, especially when the leaves turn brilliant colors in fall. In the town of Newry, just 10 minutes north, check out a classic New England photo op at the Sunday River Covered Bridge.

North Conway, New Hampshire: Panoramic Views and Plentiful Fun

About an hour’s drive to the southwest will bring you back to New Hampshire and into the lively village of North Conway. It’s an ideal place to stay, with its local shops (including the historic North Conway 5 and 10 Cent Store) and outlet malls, art galleries and plenty of dining and entertainment spots. It’s also close to Mount Washington and all of the White Mountains’ recreation options. Keep an eye on the weather forecast and set aside the clearest day to either drive or take the cog railway to the summit of Mount Washington. Be awed by the views of the rest of the Presidential Range and learn about the mountain’s famous extreme weather at the Mount Washington Observatory. Back in town, climb aboard the Conway Scenic Railroad to explore the valley, choosing either the tranquil Valley Train, which traverses babbling brooks, or the more dramatic Mountaineer, which crosses rugged Crawford Notch. At Cathedral Ledge State Park, take the short drive up to the overlook and watch for rock climbers tackling the sheer rock face, then go for a swim in quiet Echo Lake. Fifteen minutes to the north, the Wildcat Mountain Ski Area offers hiking trails to waterfalls and gondola rides to the summit in summer.

Stowe, Vermont: More Than Just a Ski Town

From North Conway, drive 2.5 hours northeast through verdant forests and hills, crossing into Vermont to reach your final destination, the year-round playground of Stowe. Its downtown is full of restaurants, boutique shopping and other comforts, while the surrounding area provides outdoor fun. Hiking and biking trails abound, including treks up Mount Mansfield, the tallest mountain in the state. The seasonal Auto Toll Road will take you to the summit by car. Alternatively, hop into a gondola for a bird’s-eye view all the way to the peak. Mount Mansfield is one of two mountains that make up Stowe Mountain Resort, a world-class resort offering over 100 trails of skiable terrain and other winter activities including dogsledding, snowmobiling, snowshoeing and ice skating. In autumn, gondola rides provide a perfect vista of all the fall colors. Smugglers’ Notch State Park is one of four state parks in the region. A scenic highway takes you through this narrow pass during warmer months, as does the Long Trail, the oldest long distance hiking trail in the nation. Find caves worthy of exploration, picnic areas and stunning views. The park’s campground provides easy access to waterfalls including Bingham Falls, Moss Glen Falls and Sterling Falls. When you’ve had your fill of Vermont’s epic outdoors, drive three hours back to Boston and fly out of Boston Logan International Airport (BOS).