11 Storybook Towns In Massachusetts
Massachusetts might be one of America's smallest states, but what it lacks in size, it makes up for with photogenic cities, towns, and villages. While Boston dominates travel headlines with its vibrant culture and popular sports franchises, several hidden gems offer the perfect dose of small-town life away from the urban hustle. These lovely communities provide an alternate travel experience, where rich scenic natural beauty, nonchalant atmospheres, and outdoor adventures dominate.
From idyllic coastal enclaves like Nantucket, where pristine sandy beaches beckon, to the serene Berkshires gems like Stockbridge, teeming with lush mountainous landscapes, these are some of the most storybook towns in Massachusetts to visit.
Stockbridge
This pretty little town in the Berkshires of western Massachusetts stands out for its spectacular natural scenery and fairytale historical mansions. Spectacular green spaces dot the community, exemplified by the Berkshire Botanical Garden. The 24-acre oasis is one of New England's oldest public gardens and displays over 3,000 varieties of plant species in a calm and soothing atmosphere. At Naumkeag, you can explore a famous local attraction that blends nature with history on a beautiful 48-acre property. It features a 19th-century Gilded Age summer home surrounded by landscaped gardens in the foothills of the Berkshire Mountains.
Stockbridge also interests art lovers with a world-class exhibition at the Norman Rockwell Museum. The venue houses an extensive collection of Rockwell's original works, from paintings to drawings.
Chatham
This historic beach town on the tip of Cape Cod houses an array of imposing landmarks as evidence of its longstanding and diverse heritage. According to the Chatham Railroad Museum, the municipality's railway heritage stretches back to 1887. The building stores multiple train cars and interactive artifacts that help preserve this rich history. Opportunities abound to document postcard-worthy sights, such as the Godfrey Windmill, listed on the National Register of Historic Places. The 18th-century wooden grist mill is one of the oldest in Massachusetts that is still in operation.
Given its proximity to the water, visitors to Chatham find their way to Ridgevale Beach for a taste of cozy coastal life. Its smooth sands and calm waters draw swimmers and sunbathers looking to chill out.
Wellfleet
Located halfway between the "elbow" and "tip" of Cape Cod, Wellfleet is the ultimate summer escape for tourists with an affinity for the beach. Its population grows sixfold during the warm season as foreigners descend upon its spectacular beaches, dramatic dunes, and toasty waters of the Atlantic Ocean. Top seaside hotspots include Marconi Beach, boasting pristine nature in every direction, punctuated by a steep cliff. The same is true for Newcomb Hollow Beach, which is unique for its imposing dunes, smooth white sand, and refreshing water.
The Great Island Trail provides a picturesque avenue for hikers to soak up Wellfleet's exotic scenery. It stretches over five miles at a high elevation and offers epic Cape Cod National Seashore vistas.
Concord
This small town, less than an hour from Boston, is steeped in history and harbors countless landmarks and sites that offer a unique perspective of the state's early years. The Minute Man National Historic Park underscores Concord's role during the American Revolutionary War. While the site hosted several battles, it is chiefly remembered for the conflict that kickstarted the Revolutionary War. The Concord Museum expertly chronicles almost four centuries of the community's history through interactive memorabilia and its far-reaching influence on American politics and culture.
Concord's colorful heritage further shows throughout its rustic downtown, where vintage mansions remind newcomers of the past eras. The Ralph Waldo Emerson House is a great example and features original furnishings and other relics stretching back to the 1830s.
Oak Bluffs
Oak Bluffs is a sought-after summer getaway on Martha's Vineyard with much to see and do, from visiting beaches and historic sites to savoring delicious seafood. Beachgoers are spoilt for options, with both Inkwell Beach and Oak Bluffs Town Beach offering the ideal stretch of sand to lounge, relax, and take in the ocean views. The island's surrounding waters are always busy, with vessels taking guests on exciting cruises for a unique town perspective. You can partake in the fun by booking a tour with Martha's Vineyard Oceansports, featuring banana boating, tubing, parasailing, and waterskiing.
Oak Bluffs is famous for its vibrant seafood scenery, evidenced by numerous eateries serving the best local flavors. Lookout Tavern's waterfront location adds to the experience of savoring luscious dishes like sauteed lobster rolls and oysters.
Sandwich
One of the oldest towns in Massachusetts, Sandwich's enduring legacy dates back to 1637 and has allowed it to amass a colorful historical heritage. It was the first community established on Cape Cod. Guests can browse an array of unique glass exhibits at the Sandwich Glass Museum as a reminder of the indelible mark the Boston & Sandwich Glass factory left on the glass-making industry in its 1800s heyday. Today, the McDermott Glass Studio does a great job preserving this heritage with an intricate portfolio of blown glass art pieces.
The Sandwich Boardwalk best represents the area's supreme natural scenery. National Geographic named it among America's best boardwalks owing to its architectural appeal and stellar panoramas of the Atlantic.
Sturbridge
This relaxed town is known for its picturesque setting on the banks of the Quinebaug River and for hosting one of New England's most fascinating living history museums. The Old Sturbridge Village spans more than 200 acres and provides a unique look into rural life in the region between the late 18th and early 19th centuries. It features dozens of original period buildings that feel like stepping into a time capsule. The Publick House Historic Inn also takes guests back to the 1770s by providing rustic accommodation in an old rural New England inn.
The Westville Recreation Area is tailored for those who appreciate living in the great outdoors. Straddling the Quinebaug River, this lovely green space has countless opportunities for hikers, picnickers, and campers.
Northampton
Northampton's distinct charm lies in its mid-19th-century flair and vibrant downtown area, where an eclectic collection of museums, galleries, restaurants, theaters, and local stores culminate in an upbeat social atmosphere. The Smith College Museum of Art holds almost 25,000 pieces of art distributed across a four-floor gallery, serving the region's cultural hub. Theater enthusiasts also congregate at the Academy of Music for a lineup of absorbing stage performances in an intimate venue that has entertained audiences since the 1890s.
From the exhibits inside Historic Northampton, the town was initially laid out in the mid-17th century. The museum boasts a 40,000-artifact catalog chronologically depicting Northampton's evolution at various periods.
Provincetown
Locally known as P-town, this Cape Cod community is historically remembered as the landing site of the Mayflower in 1620. The imposing Pilgrim Monument and Provincetown Museum have immortalized this vital piece of American history. They remind visitors of the first landfall of over 100 Englishmen and their families on what is today America. Since the late 19th century, Provincetown has lured tourists with its pristine beaches, vibrant culture, and inclusive community.
Many foreigners enjoy the laidback atmosphere of Race Point Beach, known for its magical ocean ecosystem with soft sands, turquoise waters, and dramatic sandbars. From the shore, you can enjoy storybook views of the Race Point Lighthouse, which was first erected in 1816. Besides being a photographer's dream, the landmark is a stark reminder of P-town's enduring maritime heritage.
Nantucket
Massachusetts has a fair share of island getaways, but Nantucket is often singled out for its natural allure, historical significance, and cultural vibrance. The cobblestone streets of downtown Nantucket speak to its longstanding history. At the same time, the Nantucket Whaling Museum conserves its maritime legacy with intriguing artifacts and exhibits, highlighted by a larger-than-life sperm whale skeleton. You can't miss the several lighthouses rising from the Cape Cod shoreline. At 71 feet, the Great Point Lighthouse is one of the more visible on the island, initially built in 1784.
Beaches are a significant draw in the town, and Jetties Beach ranks among the most favored. It is conveniently proximal to the urban core and offers spacious real estate with a vibrant onsite diner serving tasty seafood and cocktails.
Lenox
This cultural hub in the Berkshires charms first-timers with its lively festivals, historic estates, and stunning landscapes. Every summer since 1937, the Boston Symphony Orchestra has entertained music fans with classical and pop performances at the beautiful Tanglewood estate. Lenox's old-world mansions have always been a major point of interest for newcomers. One of the most toured estates is the Edith Wharton's Home, designated a National Historic Landmark. Set in the bucolic Berkshire landscapes, the property serves as a cultural center showcasing the life and times of the celebrated American author.
Lenox is like any other Berkshire destination, surrounded by rich natural scenery that manifests through the Pleasant Valley Wildlife Sanctuary. It boasts over 1,000 acres of meadows, wetlands, forests, at least seven miles of trail, and several native wildlife species.
Final Thought
Whether you want to slip into your swimsuit to lay back on the beach in Nantucket, lace up your hiking boots for a secluded adventure in the wilderness of Stockbridge, or stimulate your taste buds to enjoy the luscious seafood cuisine in Oak Bluffs, these charismatic towns in Massachusetts reserve a piece of the fun pie for all their visitors. They are just the right dose whenever you feel like skipping the chaotic scene in the cities of the United States.
