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8 Picture-Perfect Towns in New England

by Staff

In the picturesque landscape of rocky shores and rolling mountains, New England basks in romantic views, offering family attractions and historic landmarks such as steepled churches and old-world architecture. The “New England charm” is a real and almost palpable feeling. Choose from towns set in picturesque landscapes, such as Weston, which epitomizes New England’s countryside, or Gloucester, renowned for its history and status as one of the nation’s leading fishing ports.

Watch Hill, a ‘Gilded Age summer colony’ and a celebrity favorite, offers the perfect family escape with three immaculate beaches. Meanwhile, Woodstock is the ideal destination for hiking, boasting some of the region’s most wondrous natural features. Each town brims with its own unique local flavor and vibe. Not to mention the array of lighthouses, seafood, and the vibrant brewery scene.

Boothbay Harbor, Maine

View of Boothbay Harbor, a tourist fishing town in Lincoln County, Maine, United States, via EQRoy / Shutterstock.com

Boothbay Harbor exudes quaintness with a laid-back feel, tucked along the midcoast of Maine, offering a tranquil retreat away from the bustling Route 1. The brick sidewalks overlook the sea from the hilly terrain, where local shopping and dining experiences delight through boutiques and seaside eateries. The authentic, working waterfront enchants with a frame of rocky shores, ocean views, and marine-style opportunities, like tranquil coves and lighthouses. Take in the picturesque harborside views aboard one of its world-class boating excursions, like a sunset dinner cruise. With around 25 daily departures, visitors can explore Linekin Bay, home to seals, puffins, and whales. Additionally, the famed Pemaquid Point Lighthouse stands as a dramatic silhouette against striated rocky cliffs.

The village features attractive, hand-painted signs, as well as the Boothbay Harbor Region Sculpture Trail, offering all-season walks through public art displays of 18 sculptures. There are 300 acres of walking trails and unique, themed gardens at the Coastal Maine Botanical Gardens, complete with stonework, waterfalls, and over 35,000 blooming tulips in the spring. Visitors can enjoy easy access to the 1,000-foot-long bridge connecting the east and west sides of the harbor, as well as traditional local boatyards that continue the region’s long-standing shipbuilding tradition. In June, enjoy the boat parade and fireworks at the Windjammer Days festival, or experience the beloved Boothbay Lights Festival in winter. Don’t miss the live performances at The Opera House.

Bristol, Rhode Island

The Port at Bristol, Rhode Island.
The Port at Bristol, Rhode Island.

Bristol, an attractive town, blends abundant natural, historic, and cultural resources, nestled between Narragansett Bay to the west and Mount Hope Bay to the east. Here, everything is within a bike ride’s distance along the 10.1-square-mile peninsula, including miles of coastline, 14 parks, and downtown attractions. Perfect for a weekend getaway or a weeklong vacation, Bristol is the starting point of the East Bay Bike Path. Take a stroll along the beautiful waterfront, where historic architecture and fabulous restaurants are even more resplendent when viewed from a boat.

Thriving businesses and landscaped streets reflect great livability and tourist enjoyment. Roger Williams University adds a lively dimension to the town, with students engaged in over 40 majors, contributing to a quintessential small-town experience in an authentic New England atmosphere. Perched on Narragansett Bay, Blithewold Mansion, adorned with ornate period decor, features elaborate gardens and densely forested areas. The smaller sub-peninsula, Poppasquash, is less than 10 minutes away and is home to the top-rated Colt State Park. The Bradford-Dimond-Norris House, a cozy bed and breakfast with antique decor, features a stunning fireplace and a sunlit dining room where breakfast is served at a common table.

Franconia, New Hampshire

Franconia Notch State Park, New Hampshire
Franconia Notch State Park, New Hampshire- Image Credit Jon Bilous via Shutterstock

This charming town, nestled in the White Mountains of New Hampshire, offers an abundance of recreational opportunities, including a lake and sandy beach with mountain views. Franconia is easily explored on foot or bike. One of the region’s most photographed sites, Bridal Veil Falls, is just a hike away to the north, while Cloudland Falls and the rocky-walled, 800-foot Flume Gorge are a short drive to the south. Franconia Notch Mountain Pass is unique, nestled between 3,000-foot rock walls, and offers sweeping scenery accessible via the Cannon Mountain Aerial Tramway. You can spot the former location of the Old Man of the Mountain, a notable landmark that stood tall before collapsing in 2003, and whose memory endures on state license plates and road signs.

Tiny and sparsely populated, Franconia is an ideal place to escape the chaos of life into the beautiful outdoors, available year-round, and to visit unique sites like Robert Frost’s former home at The Frost Place. Visitors can enjoy the Cannon Mountain Ski Area in the towering mountains and an aerial tramway to Cannon Mountain. Next to the tramway, the New England Ski Museum features the local skiing legacy, including important “firsts” at Cannon Mountain and a five-time Olympic gold medalist, Bode Miller. Home to the northern half of Franconia Notch State Park, with towering trees, flowing water, and wildlife, Franconia also offers Echo Lake for fishing, paddleboarding, and canoeing.

Gloucester, Massachusetts

Historic commercial buildings on Main Street in downtown Gloucester, Massachusetts
Historic commercial buildings on Main Street in downtown Gloucester, Massachusetts, via Wangkun Jia / Shutterstock.com

From dining on delicious seafood to cultural sites and events, Gloucester has been a desirable destination for centuries. Attracting fishermen, families, artists, and globetrotters, it boasts a resplendent sea-themed shopping scene and beautiful beaches. This charming town on Cape Ann, known for its pure New England heartiness, beautiful fall foliage, and lively summers, blends the smell of the sea with the scent of oil paint along its picturesque waterfront. The picturesque harbor, home to a myriad of fishing boats and the famous ‘Crow’s Nest’ from The Perfect Storm, is an ideal starting point for exploring local culture and capturing memorable photographs.

Gloucester celebrates its history and present-day fame as one of the nation’s top fishing ports. Enjoy a sightseeing stroll and get a real taste of the fishing heritage in the food scene and working waterfront of ineffable beauty, offering a perfect North Shore experience with your loved ones! Hammond Castle Museum, an artifact-filled fantasy with a pipe organ and hidden wine cellar, and the Fisherman’s Memorial, which gazes out to sea, are must-see attractions.

Rockport, Maine

Quaint shops on a sunny day in Rockport
Quaint shops on a sunny day in Rockport. Image credit Richard Cavalleri via Shutterstock.

Rockport, a quaint town hugging a tranquil harbor, is great for families, culture lovers, and creatives. Get your first taste of beauty and inspiration at the waterfront, featuring grand schooners and bobbing fishing boats. Rockport is home to the Maine Media College, offering a Master of Fine Arts program, and boasts an extensive community of local artists. The Rockport Opera House, dating back to 1891, is a cultural cornerstone featuring music, dance, and theater performances.

The Center for Maine Contemporary Art, housed in a converted firehouse, is among the nation’s finest galleries, featuring rotating visual art displays. Open daily, Rockport Marine Park offers easy hikes, three restored lime kilns from the 1800s, and an intimate beach overlooking the bay.

Rockport is known for its many parks and the iconic marble statue of Andre the Seal, who was a local celebrity and ‘honorary Harbor Master’ for nearly two decades. Rockport Marine Park, family-friendly and perfect for picnics with harbor views, also features a locomotive replica. Walker Park is ideal for beachcombing and wading. Local artisan shops offer unique gifts and souvenirs, and numerous restaurants serve high-quality farm- or sea-to-table dishes, frequented by tradespeople, students, business professionals, lobstermen, and prestigious artists alike.

Watch Hill, Rhode Island

Luxury waterfront houses in Watch Hill Westerly, Rhode Island.
Luxury waterfront houses in Watch Hill Westerly, Rhode Island.

Watch Hill, known as a ‘Gilded Age summer colony,’ is a charming small town in Rhode Island. It has a low-key attitude and has captivated notable figures from Albert Einstein to Groucho Marx. Among the grand shingle ‘cottages’ that grace the 700 feet of beautiful shoreline is Taylor Swift’s mansion, a standout property built in 1930. From handsome shingle-style mansions to museums and a local ice cream shop dating back to 1887, it delights families and casual summer visitors with three immaculate beaches. While packed with summer vacationers, Watch Hill also serves as a great off-season escape.

From its veritable past to successfully escaping the Disney fever, Watch Hill offers plenty of ways to make memories today amid absurdly picturesque views. Join the locals in beachcombing for sea glass, visit Watch Hill Lighthouse and its small museum, and enjoy the historic Flying Horse Carousel, one of the country’s oldest, entertaining since 1883. Splurge at Ocean House, a classic wooden New England resort, command the seascape with a fabulous Sunday jazz brunch, or come for some pampering. Don’t miss the General Store at The Harbour House Inn.

Weston, Vermont

Aerial view of Weston Vermont during the colorful fall season.
Aerial view of Weston Vermont during the colorful fall season.

With the entire town listed on the National Register of Historic Places, Weston offers an old-timey vacation experience that can be enjoyed with your kids today. Weston epitomizes the New England countryside at its finest, featuring picture-perfect sights such as a resplendent town green with a gazebo, the 1832 Old Parish Church, and a waterfall at the Old Mill Museum. At the heart of town, Village Green Gallery features a cafe, handcrafted goods, and hosts concerts and other events in a picturesque setting.

Enjoy heavenly Vermont fudge, relaxed dining at local taverns, and upscale restaurants. Relive your fondest childhood memories at the Vermont Country Store, the quintessential general store restored in 1949. Offering a dizzying array of Vermont-made items, jigsaw puzzles, local cheeses, hard-to-find food, home decor, and more, it’s a must-visit. Experience all this by staying at one of the charming B&Bs near the Green Mountain National Forest, making you feel as if you’re part of a Norman Rockwell masterpiece. The artsy can enjoy a variety of plays, musicals, and concerts at the Weston Playhouse, while nature lovers have year-round access to hiking, fishing, and wildlife viewing.

Woodstock, New Hampshire

A church in Woodstock, New Hampshire.
A church in Woodstock, New Hampshire. Image credit P199 via Wikimedia Commons

There may be many Woodstocks throughout the country and even a few in New England, but none are like Woodstock in the White Mountains. This small town, bursting with local charm, is your gateway to the region’s natural wonders and the incredible outdoors. For beer tasting and good food, visit Woodstock Inn Brewery. When visiting in the summer, consider staying at the excellent private campgrounds or National Forest campgrounds. Soldier’s Park features local bands at the gazebo on Saturday nights, adding to the town’s allure. Visitors can enjoy hiking, bike rides, and scenic drives like Kancamagus Highway, which offers stunning views with plenty of pull-offs.

From Main Street, with its array of unique shops, don’t miss Cascade Park, located just behind the street. It’s a tranquil place by the Pemigewasset River, perfect for relaxing, picnicking on the rocks, and taking dips. The historic Lost River Gorge and Boulder Caves, discovered in the 1800s, feature glacial caves and a stunning waterfall. Mt. Moosilauke, just northwest of downtown, is a popular hiking area. For summertime water fun or a brilliant foliage hike to Warren Woodstock Overlook, pack your bags for North Woodstock’s Ice Castles. Featuring a hand-made castle of icicles, its incredible lighted forest walk and horse-drawn wagon rides are like something out of a fairy tale.

The Takeaway

Spanning the northeast corner of the United States, including Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont, this list features a town from each state. Pack your bags for your favorite or nearest getaway. For stunning scenery, head to Gloucester, Massachusetts, a haven for art lovers on Cape Ann, famous for its ‘Crow’s Nest’ from The Perfect Storm. Visit the memorial of a beloved seal pup, a local celebrity, in Rockport, Maine, or explore Watch Hill, a Rhode Island town known for its celebrity visitors.

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