New England Road Trip: Big-City Boston and Fresh-Air Adventures

Fly into Boston Logan International Airport and rent a car, although you may want to park it at your hotel for this first road trip stop and get around the city the way the locals do – on foot, by using Uber or Lyft, or by taking the “T” (the subway – it’s short for the Massachusetts Bay Transportation Authority, or MBTA). Begin by exploring the Boston Public Garden and Boston Common, two neighboring parks that are 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 that encompasses 16 nationally significant historic sites, including the Paul Revere House, c. 1680. 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 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 venerable Fenway Park, home of the Boston Red Sox and the oldest Major League Baseball park in the USA, then hit the road to points north.

Drive about an hour north from Boston to reach scenic Portsmouth, overflowing with historic charm from its perch on the Piscataqua River. Market Square, the traditional center of this New Hampshire port city, has architecture dating back to the 1700s. Today it’s an ideal spot to shop in art galleries and bookstores, dine on ethnic food and 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 festivals, every summer. Just across the way, the Strawbery Banke Museum brings the area’s heritage to life in 32 historic homes surrounded by period gardens and populated by costumed role players and traditional craftspeople. 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, a seaside park and beach. Take a boat cruise to the Isles of Shoals, a group of sparsely populated islands with a lighthouse and simple 1800s cottages and churches set 10 kilometers off the coast. 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.

Wind your way up the rocky Maine coast – taking a break to climb a lighthouse and admire the view – 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 coast; or drive the Park Loop Road, pausing to watch the waves crashing at Thunder Hole and take photos of the Cranberry Isles just offshore. For a quintessentially Maine experience, take a cruise on the Lulu, a traditional Down East lobster boat, to get a firsthand look at lobstering, watch for seals and enjoy postcard-worthy sights of the Maine coast. At the end of the day, sample fresh lobster in a waterfront restaurant back in Bar Harbor. In the morning, drive west into the mountains to reach the village of Bethel.

Set among western Maine’s lakes and mountains, Bethel is a quaint village with a walkable downtown full of shops, restaurants and bed-and-breakfast inns. This picturesque village is located just minutes from some of the state’s best outdoor recreation options, making it a perfect basecamp for adventurers. 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, set on the banks of the Androscoggin River, visitors can rent canoes, kayaks, tubes or stand-up paddleboards and go paddling among the Mahoosuc Mountains watching for moose, deer, eagles and river otters. Other options there include sluicing for precious and semiprecious gems and minerals and walking across the 150-meter-long Burma pedestrian suspension bridge to Hastings Island, where you can follow a trail to see birds and other wildlife. Drive 20 minutes from Bethel to Grafton Notch State Park and hike through spectacular gorges to scenic peaks and waterfalls including Screw Auger Falls and Mother Walker Falls. The park is home to a portion of the Appalachian Trail, so watch for thru-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 quintessential New England photo op at the Sunday River Covered Bridge, built in 1872.

About an hour’s drive to the southwest will bring you into New Hampshire and to 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) and outlet malls, art galleries and plenty of dining and entertainment options, as well as its close proximity 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 famously extreme weather at the Mount Washington Observatory Weather Discovery Center. 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.

From North Conway, drive 2.5 hours northeast through lively forests and hills, crossing into Vermont for your final destination, the year-round playground of Stowe. Its downtown is full of restaurants, boutique shopping and other comforts, while the area surrounding provides outdoor fun in every season. 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, or 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. This world-class resort offers 116 trails of skiable terrain and other fun winter activities including dogsledding, snowmobiling, snowshoeing and ice skating. In autumn, gondola rides up the mountains provide a perfect view 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, or you can hike it via Long Trail, the oldest long distance hiking trail in the nation, which runs 439 kilometers from Vermont’s southern border with Massachusetts straight north to Canada. 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 3 hours back to Boston and fly out of Boston Logan International Airport.