10 Small Towns In Massachusetts To Visit For A Weekend Getaway

Massachusetts enjoys its share of fame and infamy, from whaling in Nantucket to the summer playground of the Gilded Age in Lenox, and from the heart of the American Revolution in Concord to the art of Norman Rockwell in Stockbridge. Its storied history has left a trail of charming small towns from the shores of Cape Cod to the pastoral hills of the Berkshires.

Whether you are looking for arts and culture, stolen moments reconnecting with nature, or time to explore New England’s storied history, here are 10 small towns in Massachusetts to visit for a weekend getaway.

Stockbridge

Stockbridge’s tranquil Berkshires location on the banks of the Housatonic River earned it a place on Architectural Digest’s most beautiful towns in America list. Its proximity to Albany, Boston, and NYC offers a convenient weekend getaway.

The Stockbridge Country Inn’s historic lodging is the quintessential New England stay in a 1856 Federal colonial house set against lush acreage and charming gardens. Each room is designed to capture the distinct furniture and décor of the period, where guests relax in their private quarters or snuggle up in the inn’s inviting spaces. It is also within walking distance of Stockbridge’s most popular destinations.

Stroll over to the Norman Rockwell Museum to discover the powerful imagery that has come to define American life. The collection of almost 1,000 original paintings and drawings features the warmth and humor of the renowned artist. You can also explore Rockwell’s authentic art materials and personal items at his Stockbridge studio.

Head to the Lost Lamb for tantalizing sandwiches on French baguettes and a few indulgent sweet treats to go. Afterward, wander the beautiful grounds at Berkshire Botanical Gardens.

Experience the culinary delights and superior wine list in the beautifully appointed Red Lion Inn’s main dining room under a shimmering crystal chandelier. Settle in for a restful sleep back at the inn. Awaken refreshed for a made-to-order breakfast, from waffles and pancakes drizzled in Vermont pure maple syrup to hearty platters of bacon and eggs.

Sturbridge

Sturbridge’s central location, about 50 miles from Boston, Hartford, and Providence, earns it the title of the “Crossroads of New England.” Plenty of Yankee history and picturesque woodlands create an idyllic Massachusetts getaway. Elm trees planted in 1791 shade the Publick House Historic Inn. The guest rooms offer 18th-century décor with modern comforts, where period-appropriate furnishings embrace New England’s history.

Lunch at the inn’s Tavern taking in the historic ambiance while dining on traditional tavern fare. Embrace town history at Old Sturbridge Village, where costumed historians wander over 200 acres and share stories in the 40 historical buildings. Travel back to the 19th century, where food simmers over open hearths and hardworking villagers carry on with daily chores, including blacksmiths, potters, cabinetmakers, and printers.

Sip drinks fireside at the hotel before dinner beneath a cozy post-and-beam ceiling at the Inn’s original dining room. The six-foot open-hearth fireplace crackles away cheerfully while guests feast on traditional roasted turkey dinners or hearty Yankee pot roast. Retire to your room and snuggle into bed.

In the morning, grab a famous pecan sweet roll and coffee at the inn’s 18th-century Bake Shoppe before heading out for a morning hike. Experience the natural splendor of Opacum Woods along four miles of hiking trails through diverse scenery, including a pond, riverlands, farmland, and forests. Stock up on fresh delights from local farmers and food makers at the Sunday Sturbridge Farmers Market for the drive home.

Nantucket

Lovely Nantucket is an island getaway off the coast of Cape Cod, accessible via ferry from New Bedford, NYC, and Hyannis. Views as you approach the island offer a hint at the beaches, lighthouses, and historic architecture awaiting your discovery.

The iconic Union Street Inn is the go-to destination for in-the-know travelers looking for the ultimate New England experience. The inn’s history, elegance, and unmatched style offer period authenticity in every room.

From 1924 to 1943, members of the Nantucket Art Colony frequented the cobblestone streets. Today, galleries and museums dot those streets, including the Cecelia Joyce and Seward Johnson Gallery. Discover emerging talent at their changing artist exhibitions or participate in artist-led demonstrations and lectures. The Whaling Museum also offers a compelling mix of art and insights into the island’s dramatic whaling history.

Dine at one of the island’s most beloved restaurants, Seagrille, where the food, wine, and cocktails feel upscale, and the inviting dining room and staff are all about cozy comforts. Retire to your sumptuous room at the inn and sink into a well-deserved sleep.

Awake to the tempting smells of an enticing breakfast wafting up from the dining room streaming with sunlight. Gobble up decadent blueberry pancakes, eggs done any way you like them, or lighter fare overlooking the water. Stroll along the beach taking in the sweeping views before boarding the ferry back to the mainland.

Oak Bluffs

Oak Bluffs’ picturesque spot on Martha’s Vineyard is reached via ferry from towns including Hyannis or Woods Hole. The town’s historic sites are its best feature, making its northeast shore location feel more charming than bougie.

The Oak Bluffs Inn is a restored 1870 Victorian home with a distinctive period turret and comfortable white wicker chairs on an expansive front porch. The Carriage House offers a separate entrance off a peaceful garden where intimate quarters capture a casual coastal vibe.

Your room is within strolling distance of a former summer campground, where you can explore the island’s famous gingerbread cottages. The cluster of ornate, whimsical cottages is a reminder of island summers in the 1800s, and you can tour a typical cottage decorated in period furnishings at the museum. Continue your 19th-century journey riding America’s oldest platform carousel. The fanciful, hand-carved, colorfully painted Flying Horses, once found at Coney Island, moved to Martha’s Vineyard in 1884.

Dine on warm bowls of authentic New England-style clam chowder and lobster rolls at Martha's Vineyard Chowder Company, and sip craft beers and cocktails on the front porch before heading back to the inn.

In the morning, you are steps from your continental breakfast at the main house. End your weekend stay wandering the shoreline at Oak Bluffs’ sandy beaches to admire the tranquil ocean views.

Concord

Historic Concord is the site of the first battle of the American Revolutionary War. If you love American history, this is the weekend getaway for you, just 20 miles from Boston. The main rooms at Concord’s landmark Colonial Inn include features dating back to the early 1700s, making it the perfect base for your New England history lesson. The town’s many walking tours cover snippets of America’s past, from Black History to the famous women of Concord, and kid-friendly tours to major contributing businesses that helped establish the local economy.

Have lunch at Helen’s Restaurant, where three generations of cooks have satisfied the changing cravings of their guests since the early 1930s. Order old-school diner-style favorites or something from their ever-changing latest additions. Then head to the Concord Museum for a fascinating look at the American Revolution with a collection of weapons and artifacts, including one of two lanterns Paul Revere used to signal the advance of the Redcoats.

Dine on American classics, soaking up the history back at the inn, and have evening drinks on the lovely patio. Take an after-dinner stroll in town or snuggle up with a good book in your room.

After breakfast at the inn, switch gears to explore the town’s ties to American literature. The guide-led Emerson-Thoreau Amble follows the path often strolled by friends, philosophers, and writers Henry David Thoreau and Ralph Waldo Emerson. Catch glimpses of the landscape that inspired their work and teachings, from Walden Pond to Henry’s cabin site.

Wellfleet

Wellfleet sits on the Outer Cape between Cape Cod Bay and the Atlantic Ocean, just over 12 miles from Provincetown. The town’s coastal whimsy instantly sets your mind at ease as you settle into your weekend sojourn.

The Copper Swan boutique hotel’s location on Duck Creek offers tranquil bay marsh views and 22 well-appointed rooms celebrating the warmth and beauty of Cape Cod hospitality. The moment you step into the reception area at the Captain’s House, you will know you have discovered something special. If you can tear yourself away from your lovely room, a calming stroll through the Mass Audubon Wellfleet Bay Sanctuary reveals a changing landscape from shaded woodlands to salt marshes and freshwater ponds to sandplain grasslands.

Wellfleet is known as “the art gallery town” and for summer gallery strolls on Saturday evenings. If you visit in the summer, this is a wonderful way to explore the town after dinner at Winslow’s Tavern. The spacious patio sheltered by shady trees is the place to dine on summer evenings. The lovely inn’s white clapboard house and charming black shutters are a downtown landmark where fresh seafood reminds you why you chose a Cape Cod getaway.

After strolling the galleries, sink into a comfy deck chair at the hotel before heading up to bed. Have your complimentary continental breakfast on their patio and stroll downtown to shop the quaint boutiques or visit the Wellfleet Historical Society Museum to explore the collection and exhibitions.

Lenox

Lenox is tucked away in the Berkshires, where unique stays are all about country charm. Stonover Farm does not easily give up its secrets with its humble 1890s farmhouse façade. However, when you step into your guest room, you will discover the meaning of rustic-chic. Explore life during the gilded age at the artisan-crafted Jacobean-Revival mansion, Ventfort Hall. The Gilded Age Museum reflects the opulent lifestyle of the richest of the rich and often hosts elegant Victorian Teas. Follow the opulence theme to The Mount, built by the famed author Edith Wharton in 1902. The imposing mansion sits on manicured grounds and serves lunch overlooking the garden at the Terrace Café.

Have dinner at the 1899 Appletree Inn, where drinks and live music at The Ostrich Room are the main attraction. The warm, inviting atmosphere and infectious music are made all the more delightful with the inn’s period features, including chunky wood beams and a crackling fire complete with cozy inglenook seating.

Sink into peaceful sleep at the farm and spend your morning relaxing by the duck pond with a cup of coffee after your full, cooked-to-order breakfast in the Creamery or Courtyard. Immerse yourself in the splendor of the Berkshires at Pleasant Valley Wildlife Sanctuary, where trails wend through over 1,000 acres, or take the strenuous climb to breathtaking views of Mount Greylock, the Taconic Range, and the Catskills.

Chatham

Chatham is about 85 miles from Boston on the southeastern tip of Cape Cod’s "elbow." The town's tiny 16 square miles offer restful views on all sides, surrounded by the Atlantic Ocean, Nantucket Sound, and Pleasant Bay.

Check in at the Chatham Bars Inn, where the thoughtfully restored rooms have all the charm of a historic inn and the amenities of a boutique hotel. The downtown location is close to both the village shops and white, sandy beaches.

Sample the elevated lunch menu at the inn’s shaded, breezy Veranda restaurant, admiring the views before taking a long walk. Amble the picturesque streets while shopping the quaint boutiques, and treat yourself to scrumptious confections at Chatham Candy Manor. Rent bikes to explore the town and beach trails or kayaks to take in the shoreline from the water. In the late afternoon, watch the seals follow the fishing boats back to town.

Luxuriate at the inn’s spa, where their trademark treatments offer first-class pampering before cocktails back at the Veranda. After a sumptuous dinner, check out the movie listings at the vintage Orpheum Theater, where you might catch a classic film. Slip into slumber in your luxe room and wake up extra well-rested. Drag yourself from your warm bed and drive down to the beach to watch the sunrise before breakfast at the inn’s Stars restaurant. Indulge in exceptional dishes in sophisticated surroundings overlooking the harbor dotted with colorful fishing boats.

Sandwich

Sandwich is the oldest town on Cape Cod, sitting on the northwest corner, just over 50 miles from Boston. The village architecture ranges from humble, quaint cottages to impressive, ornate mansions of seafaring captains.

The Belfry Inn & Bistro offers truly unique stays at the Abbey, where wood-clad sloped ceilings are a standout feature, and the “Tuesday” room includes a breathtaking stained-glass window.

Explore the delicate beauty of Sandwich’s ties to the glass industry at the Sandwich Glass Museum to admire original pieces created during the 1800s. Known as the town that glass built, you can watch glassblowing demonstrations and discover glassblowers' studios throughout the village, including McDermott’s backyard studio.

The historic Sandwich Boardwalk is known as the “Plank Walk” for a reason. Running about 1,300 feet in length, the weather-worn planks take you across Mill Creek and marshlands to the Town Beach on Cape Cod Bay with lovely scenic views along the way. After a day of exploring, enjoy an indulgent dinner at the Inn’s converted 1901 church, where the original stained glass, imposing oak buttresses, and choir balcony offer an eclectic backdrop for the chef-crafted menu. Sip après-dinner drinks in one of the bistro’s cozy alcoves before a restful sleep in your Abbey room. In the morning, visit Heritage Museums & Gardens to explore the grounds, exhibits, and a full-scale reproduction of a traditional Wampanoag dwelling and vegetable garden.

Williamstown

Williamstown is a quaint college town in northwestern Massachusetts, bordered by Vermont and New York. The picturesque buildings of the Williams College campus have a classic caps and gowns vibe steeped in the country charm of the Berkshires.

The Williams Inn’s contemporary architecture embraces the modern farmhouse style with a warm stone and wood façade nestled against the scenic landscape. The sophisticated guestrooms are light-filled and elegant with just enough rustic features to offer a warm embrace.

This college town is all about the culture, including The Clark Art Institute. This leading international art museum explores the nature of art and art history. The pebble-strewn pond at The Clark Center captures the building’s reflection, creating a striking image and serene views when touring the galleries. Nab a surprisingly good Lobster Roll at the center's laid-back Café 7 -- if they are not sold out, that is. Admire the edgy concrete, streaming natural light, and mid-century modern vibe with a glass of wine.

Return to the inn for dinner and drinks at the Barn Kitchen & Bar for classic New England favorites, and sit out back in a comfy fireside deck chair looking at the night sky. Sink into your luxurious bedding for a well-earned sleep and enjoy a freshly-made breakfast at the Barn in the morning. Drive to Bennington Museum to discover New England history and the iconic folk paintings of Grandma Moses before heading home.

Whether you are in dire need of a last-minute escape or prefer a carefully planned weekend away, these New England towns provide the perfect base to explore Massachusetts. Inspired galleries, inventive eateries, warm, cozy inns, and historic sites await at these 10 small towns in Massachusetts to visit for your next weekend getaway. So mark the date on your calendar or pack up the car for an adventure in America's Bay State.