6 Cutest Small Towns To Visit In Massachusetts

These six cute towns in Massachusetts offer quintessential New England charm. From Chatham's scenic beaches to Stockbridge's Norman Rockwell-inspired streets and Nantucket's pristine shores, each town has its own unique allure. Colorful cottages in Oak Bluffs, a historic lighthouse in Newburyport, former “summer’s cottages” in Lenox, and festivals like Nantucket Race Week, Harborfest, and Tanglewood only add to the allure. Whether strolling through historic streets, relaxing on sandy beaches, or enjoying cool festival vibes, these six towns promise an unforgettable taste of Massachusetts' beauty and hospitality.

Chatham

On the “elbow” of Cape Cod, Chatham boasts scenic beaches, historic lighthouses, and a cute downtown area with boutiques, art galleries, and seafood restaurants like Impudent Oyster and the recently-renovated Wild Goose Tavern. Visitors can explore the iconic Chatham Lighthouse—one of the few lighthouses in the U.S. operating 24 hours a day. A short mile away, visitors can add on a tour of the 7,921-acre Monomoy National Wildlife Refuge, which protects habitats critical to the survival of migratory birds, horseshoe crabs, tiger beetles, gray seals, and other wildlife.

Another worthwhile site to visit in Chatham is the Shark Center (or the Atlantic White Shark Conservancy), where you can learn about the area’s most popular summer visitor, the great white shark. Book a Receiver Tour and spend an hour cruising Chatham Harbor, learning about ongoing shark conservancy efforts.

Chatham hosts its premier event, the 53rd Festival of the Arts, held August 16 - 18. The festival has been called a “rite of summer” by the Cape Cod Chronicle. The juried, high-quality festival celebrates the work of 120 artisans presenting original artwork, glass, pottery, and more. The family-friendly festival features a children’s arts and crafts tent, a shuttle bus service, and food trucks to accommodate a crowd of around 10,000 visitors.

Stockbridge

Very few towns can claim to be as cute as Stockbridge. Renowned for its picturesque Main Street lined with galleries and shops, Stockbridge is best known as the setting for Norman Rockwell's iconic paintings. The downtown portion of Main Street was the setting for his 1967 painting, “Main Street, Stockbridge at Christmas.”

Visitors to the town will definitely want to see the Norman Rockwell Museum, with its ten galleries, all 323 of its The Saturday Evening Post covers, and explore the scenic 36-acre campus. Events and special exhibits at the museum include a “Community Dog Day” inspired by the illustrator’s love for dogs and the “MAD Bash” celebrating MAD magazine's fun and irreverent humor.

Another must-see stop on any tour of Stockbridge is Naumkeag—a public garden and Gilded Age historic home in the heart of the Berkshires, Massachusetts. The 48-acre architectural masterpiece was once the summer retreat of the U.S. Ambassador to Great Britain. The estate hosts numerous events throughout the year, including the annual Daffodil & Tulip Show and the Naumbeag Pumpkin Show, with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins, and countless locally grown gourds.

Oak Bluffs

Oak Bluffs is a charming town on Martha's Vineyard's northeastern shore and the quintessential New England summer retreat. It is known for its colorful gingerbread cottages, beautiful beaches, and bustling harbor area. It's a favorite summer destination for its relaxed atmosphere and historic landmarks like the Flying Horses Carousel, the oldest platform carousel in the U.S. The carousel was moved to Oak Bluffs in 1884 from Coney Island and includes hand-carved wooden horses with manes and tails of natural horsehair and inset glass eyes.

The Joseph Sylvia State Beach is a two-mile stretch of soft sand and shallow water. Due to its gradual slope into deeper water and small waves, it is a famous beach for families. In addition to swimming, visitors can surf fish for striped bass from the beach or bait fish from the American Legion Memorial bridge (also known as the “Jaws Bridge” because the bridge served as a filming location for the classic 1975 film Jaws).

The 31st Annual Harbor Festival, known as “HarborFest” to the locals, takes place in June and hosts 60 local vendors and nine musical performers. HarborFest invites Island residents and more than 1,000 visitors each year to walk, taste, and shop their way through Oak Bluffs. It features kid- and family-friendly events, including a Chalk Walk and a Sandcastle Contest. The event is free and open to the public.

Newburyport

Newburyport along the Merrimack River features a scenic waterfront, historic neighborhoods with Federal-style houses, and a lively downtown with carefully curated boutiques and eateries. The phrase “Shop Local” is widely embraced here, so be sure to explore stores at the Tannery Historic Marketplace, such as Jabberwocky Bookshop, Wishbasket, and Henry Bear’s Park, which offer a wide range of children's gifts. From February through December, the town hosts “First Fridays,” where shops remain open late every Friday to support the local economy.

The Plum Island Lighthouse (also known as the Newburyport Harbor Lighthouse) was constructed in 1788 and was the 13th lighthouse in the U.S. The last keeper left in 1951, but thanks to automation, a flashing green light still guides boats safely through the spot where the Merrimack River meets the Atlantic Ocean. 15-minute tours of the lighthouse are available only by request.

On the road back from Plum Island, outdoor enthusiasts will want to stop at Parker River National Wildlife Refuge, which offers a 6.4-mile network of trails for hiking, walking, and jogging. Most of the refuge comprises salt marshes, and the best way to experience it is by paddling by canoe, kayak, or paddleboard, which visitors can launch directly from the beach. Surf fishing for flounder, bluefish, and striped bass is also permitted (with a valid license).

Lenox

Lenox is a quaint town located in the Berkshires of Western Massachusetts. In the early 1900s, it was called the “Newport of the Berkshires,” where the wealthy, including the Astors and Vanderbilts, vacationed in their 30-room mansions known as “cottages.” Many of these summer estates still stand, now serving as hotels or museums. The charming downtown area features unique shops, galleries, and eateries. The Bookstore & Get Lit Wine Bar offers a delightful combination of new and vintage books with wine tastings; Haven Café and Bakery is popular for weekend brunches with eggs benedict and mimosas; and Shots Café is perfect for a morning latté and a warm pastry.

The town of Lenox is synonymous with music, and every summer, the small town welcomes over 350,000 visitors to Tanglewood—the beloved, well-known music festival. It is also the summer home of the Boston Symphony Orchestra (BSO), the Tanglewood Music Center, and the Boston Pops and has been hosting concerts and events since 1937. The Tanglewood season will feature more than 100 performances, including eleven weeks of concerts and other events, including recitals, chamber music, and performances by the Boston Symphony Orchestra, the Boston Pops, and Boyz II Men, to name a few. The highlight of this summer’s festival is the 50th-anniversary performance of James Taylor and his All-Star Band on July 3 and 4.

Nantucket

Nantucket, renowned for its white sandy beaches, is a picturesque New England town that can be challenging to reach since visitors must travel by ferry or plane. Nonetheless, it’s worth the effort. Popular beaches include Jetties Beach, Surfside Beach, and Madaket Beach, where visitors can enjoy sunsets and later dine at Madaket Millies. The island's extensive bike trails make exploring easy, allowing trips to places like Brotherhood of Thieves for a lobster roll and a soda from their bottomless fountain.

Summertime means festival time in Nantucket, with two back-to-back events occurring on the small island in June. The Nantucket Book Festival will take place from June 13 to 16, and its line-up includes authors Kwame Alexander, Paul Harding, and Eric Larsen. The following week, June 19 - 24, the town welcomes the Nantucket Film Festival—one of the premier destination film festivals in the world. In August, the town holds its annual Nantucket Race Week, which features a series of sailboat races and regattas in Nantucket Habor and Sound.

Plan Your Visit Now

Discover classic New England charm by visiting these charming towns in Massachusetts. Stroll through lively downtowns with boutique shops, art galleries, and delicious seafood eateries. Immerse yourself in cultural activities, from museum visits celebrating famous artists to outdoor concerts and festivals. Enjoy waterfront scenery along the Merrimack River or take a walk on sandy beaches overlooking the Atlantic. Combining historic sites, natural beauty, and vibrant events, these towns offer a memorable escape.