6 Cutest Small Towns In Massachusetts To Visit In 2024

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, 2024. 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 in 2024 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 2024 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

Along the Merrimack River, Newburyport offers visitors a picturesque waterfront, historic neighborhoods with Federal-style homes, and a bustling downtown area with beautifully curated boutiques and restaurants. “Shop Local” is a popular term in the cute downtown area, so be sure to visit the shops in the Tannery Historic Marketplace, like the Jabberwocky Bookshop, Wishbasket, and Henry Bear’s Park, for a great selection of children's gifts. From February to December 2024, the town hosts “First Fridays,” where shops stay open late every Friday to encourage the town’s 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 small town nestled in the Berkshires of Western Massachusetts. In the early 1900s, it was referred to as the “Newport of the Berkshires,” where the wealthy, like the Astors and the Vanderbilts, retreated to relax in their 30-room mansions called “cottages.” Many of these summer homes remain but have been reimagined as hotels or museums. Lenox’s charming downtown streets have unique shops, galleries, and restaurants. The Bookstore & Get Lit Wine Bar is a fun mix of new and old books paired with wine tasting; Haven Café and Bakery is a great spot for an eggs benedict and a mimosa brunch on weekends; and Shots Café 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 2024 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

Famous for its white sandy beaches, Nantucket is a beautiful New England town that may be a bit difficult to reach, as visitors can only get there by ferry or airplane, but it’s well worth the effort. The most popular beaches include Jetties Beach, Surfside Beach, and Madaket Beach, where visitors can watch the sunset and follow it up with a post-sunset dinner at Madaket Millies. Nantucket’s extensive bike trails make traveling anywhere on the island possible, like Brotherhood of Thieves for a lobster roll and drink from their bottomless fountain soda.

Summertime means festival time in Nantucket, with two back-to-back events occurring on the small island in June 2024. 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

Experience quintessential New England charm by visiting these cute towns in Massachusetts. Explore vibrant downtown areas filled with boutique shops, art galleries, and delectable seafood restaurants. Enjoy rich cultural experiences, from museum tours celebrating renowned artists to outdoor concerts and festivals. Indulge in waterfront charm along the Merrimack River, or take a beach walk on sandy shores overlooking the Atlantic. With a blend of historic landmarks, natural beauty, and lively events, these towns promise an unforgettable getaway.