11 Small Towns in Massachusetts to Visit for a Weekend Getaway

Massachusetts, with its rich combination of history, culture, and natural beauty, is home to a host of must-visit destinations for a rejuvenating weekend getaway. From the literary appeal of Concord to the coastal vibe of Chatham, each town presents an opportunity for relaxation. Whether you are a history enthusiast, an art connoisseur, or simply seeking seaside serenity, Massachusetts has the ideal retreat for you. Learn about some of the wonderful places to escape for a weekend in the Bay State.

Concord

Those with a love for literature and history may deem the eastern Massachusetts town of Concord just right for a quick break from daily life. Discover the Orchard House, a living monument dating between 1690 and 1720, where Louisa May Alcott authored "Little Women." Explore the rooms where the prolific author wrote this 2-volume, classic piece of literature.

But before your literary adventure, choose from one of the 56 well-appointed guest rooms available at The Colonial Inn. The hotel is conveniently located near major suburban Boston highways. Alternatively, The North Bridge Inn, a bed and breakfast, is in the heart of downtown Concord, near Monument Square, just a brief stroll away from Concord Main Street.

Of interest to outdoor enthusiasts, the Walden Pond Path allows visitors to savor the natural beauty that inspired transcendentalist thinkers Thoreau, Emerson, and Hawthorne, while the nearby Minute Man National Historical Park traces the American Revolution.

To round off your days of exploration, check out the Woods Hill Table for farm-to-table meals or Fiorella’s Cucina for authentic brick oven-prepared dishes.

Rockport

Whether you are an artist or an art fan, Rockport is the ideal weekend respite. Just an hour north of Boston, this town offers a breath of fresh salty air along the coastline, enchanting visitors and residents alike with its rugged beauty. Known for its vibrant art scene, Rockport is home to 30 galleries, including the Mercury Gallery and The Art Nook, where visitors can explore and purchase one-of-a-kind pieces crafted by local artists.

To satisfy your appetite, try the Roy Moore Lobster Co. for fresh seafood or Feather and Wedge for seasonal menus and live music. Consider the recently updated Emerson Inn for an inviting stay with luxurious rooms and spectacular ocean views.

Get outside and take in the unbridled beauty of Halibut Point State Park, featuring rocky cliffs and Atlantic views. Rockport also hosts various outdoor events, including concerts, festivals, and celebratory events such as the Rockport New Year’s Eve Celebration, providing a chance to participate in the lively local community and culture.

Lenox

Lenox, located in the Berkshires, is a treasure trove of Gilded Age history, and a visit to the Ventfort Hall Mansion provides a glimpse into this opulent era of rapid prosperity. This historic mansion, with its stunning architecture, serves as a museum, offering guided tours that unveil the lavish lifestyle of the Gilded Age elite. For an upscale dining experience, you may appreciate the Alta Restaurant and Wine Bar, featuring Mediterranean cuisine made with local ingredients.

To fully engage in the town's charisma, a stay at the Birchwood Inn Bed and Breakfast could be just what you need. It is an exemplary accommodation option for a relaxing retreat with 11 modern luxurious rooms with a historic ambiance.

You will also have opportunities for outdoor activities while in Lenox. Put on your hiking gear and head over to Kennedy Park, where there are hiking trails that wind through scenic woodlands. Also, for your entertainment, Tanglewood, an acclaimed music venue set in the beautiful Tanglewood Music Center, hosts outdoor concerts and events, featuring an eclectic selection of musical performances from classical to jazz to contemporary pop.

Salem

Museum aficionados might want to pay attention. Salem, located in northeastern Massachusetts, is particularly renowned for the notorious witch trials. However, it is also the home of the oldest museum in continuous operation in the United States! The Peabody Essex Museum, first opened in 1799, contains artifacts from all over the world.

Another notable site you do not want to miss is the House of the Seven Gables, a mansion with a storied past dating back to the 17th century, providing insights into Salem's colonial history and American novelist Nathaniel Hawthorne's literary legacy. When dinner time rolls around, check out Turner's Seafood, for satisfying New England-style seafood cuisine.

End your day with an evening of rest at The Merchant Hotel, whose building dates to 1784 as a tavern and transitioned to an office building and then a rare book shop before it was a boutique hotel with 11 exquisitely designed guest rooms. For outdoor events, the Salem Maritime Festival presents live music and opportunities to try your hand at crafts such as ropemaking and soapmaking.

Stockbridge

Stockbridge invites visitors to step into the timeless scenes depicted in Norman Rockwell's iconic paintings. Take in a production at one of the four stages of Berkshire Theatre Group. For a taste of classic New England cuisine, dining at the historic Red Lion Inn, dating back to the 18th century, is a must.

Outdoor enthusiasts can explore the nearby Stockbridge Bowl, an awe-inspiring lake offering opportunities for water activities and hiking along its shores. Additionally, the town hosts events like the Stockbridge Main Street Christmas celebration, where the charming streets come alive with festive decorations, reflecting the town's warm and welcoming atmosphere.

Newburyport

Newburyport radiates coastal New England charisma, steeped in nautical tradition. The town, located in the northeast corner of the state, presents a multitude of occasions for a weekend respite. Explore the Tannery Marketplace, a conglomeration of more than 40 businesses for dining, shopping locally crafted goods, and exploring your own creativity, crafting your own one-of-a-kind souvenir at establishments like The Artists’ Playground.

Unwind with a stay at The Essex Street Inn, a designer hotel in the heart of downtown. Walk off some energy and breathe in the fresh air on Clipper City Rail Trail. You will enjoy the unique trail, lined with sculptural works of art by artists Scott Kessel and Matt Niland. The town's waterfront area hosts outdoor events such as the Newburyport Farmers' Market, providing a platform for local vendors and artisans.

Additionally, you will want to take a walk along the pristine sandy beaches of Plum Island. If you do go, be sure to bring your binoculars for birdwatching and keep a look out for the many bird species you may encounter, such as a black-capped chickadee,  great blue heron, or even an American bald eagle.

Plymouth

As pivotal a place as Plymouth holds in American history, there is much more to do than visit the famous Plymouth Rock. For example, if you desire a break from the usual, you could consider a harbor cruise on a classic paddlewheel boat with Pilgrim Belle Cruises. Moreover, Plymouth hosts an array of outdoor events, such as the Plymouth Waterfront Festival, celebrating the town's seaside heritage with live music, food vendors, and family-friendly adventures. You can take advantage of the opportunity to get the whole family outside to trek the waterfront terrain and fascinating landmarks of Plymouth Harbor Trail. Also, not to be missed, Plymouth's beaches, including Long Beach and White Horse Beach, provide opportunities for much-needed relaxation.

For your dining pleasure, the East Bay Grille serves up a plethora of meal choices, from steak to seafood and pasta, with waterfront views. For your weekend away in Plymouth with a touch of luxury, the Mirbeau Inn & Spa Plymouth presents a sophisticated retreat. This French manor-style boutique inn encircling the Monet Pond gardens provides top-rated accommodations, with an onsite wine bar and a tranquil spa rendezvous.

Marblehead

Take a break from the everyday routine and become engrossed in the sailing heritage and rich maritime history of Marblehead, situated on the North Shore of Massachusetts. Many towns in Massachusetts are steeped in historical importance, and Marblehead is no different. Fans of period architecture will not want to miss an exciting and informative tour of the Jeremiah Lee Mansion. The well-preserved mansion, dating back to the 18th century, highlights Georgian architecture and provides insight into Marblehead's prominence as a fishing capital of Massachusetts and the origin of Marine Corps Aviation.

While you are in the mood for all things marine-related, consider The Landing Restaurant for its sea-inspired menu and scenic waterfront setting. For engaging family outings, why not visit the Neck Wildlife Sanctuary, which features walking trails with magnificent views of the coast and opportunities for birdwatching?

If you are in the mood for musical entertainment, the Marblehead Festival of Arts presents local artists annually during the summer. For a weekend stay that encapsulates Marblehead's seafaring legacy, the Harbor Light Inn, a historic bed and breakfast, features select rooms with jetted spa tubs and fireplaces.

Amherst

Amherst presents an exceptional location for a weekend getaway for the poets and poetry lovers among you. Spend an afternoon in quiet reflection as you visit the Emily Dickinson Museum, located in the poet's former residence. Become absorbed in an intimate look into her life and the works that preserve the legacy of this literary icon. The town also caters to outdoor events with the Robert Frost Trail, offering energizing hiking opportunities through woodlands and meadows.

Participate in community engagement at the Amherst Arts Night Plus, featuring art exhibitions and live performances. When hunger strikes, savor farm-to-table cuisine at 30Boltwood, an upscale restaurant known for its commitment to locally sourced ingredients. Find restful lodging at the eco-conscious Inn on Boltwood, with comfortable and welcoming rooms overlooking Amherst Common.

Chatham

What is more relaxing than the sound of the ocean waves and the feel of fresh salty breezes? No matter your location in the town of Chatham on the southeastern tip of Cape Cod, this is sure to be your prevailing atmosphere. Those looking for retail therapy will enjoy a stroll down Main Street, where there are shops, such as the Fisherman’s Daughter for clothing and the Mayflower Shop for home goods.

If you have a craving for seafood, look no further than The Impudent Oyster. With an air of quirkiness, the structure, formerly a church serving a congregation, now is a popular restaurant that serves up fresh seafood in a lively atmosphere featuring an in-house bar.

Take time to walk along the beach and stop by the Chatham Fish Pier, where visitors can observe the daily catch and enjoy the energetic atmosphere of this waterfront hub. For a memorable place to stay, look to Chatham Bars Inn. You will be lulled to sleep nightly with views of the Atlantic at sunset and the rhythmic lapping of waves nearby.

Williamstown

Williamstown could be the ideal retreat for the art lover who is desiring time for quiet reflection. Located in the Berkshires of northwestern Massachusetts, Williamstown is a vibrant cultural hub. For example, you will want to visit The Clark Art Institute, which houses an extensive collection of European and American art, with works ranging from the Renaissance to contemporary pieces. Take your time meandering through the museum's galleries and outdoor spaces, including the serene reflecting pool.

Afterward, grab a fixed-price, 3-course meal at the Mezze Bistro, known for its inventive menu highlighting locally sourced ingredients. For a restful stay where you can unwind, The Williams Inn has you covered with 64 beautifully equipped rooms, a full-service on-site restaurant, and a fitness center.

Massachusetts is a treasure trove of opportunities for your weekend escape. From the literary havens of Concord to the maritime elegance of Marblehead, each town offers a chance to create lasting memories. Whether you take solace in the quiet reflection of Emily Dickinson's world in Amherst, savor the coastal delights of Chatham, or dive into the cultural depth of Williamstown, Massachusetts unfolds as a multifaceted destination for weekend escapades. So, pack your bags and embark on a journey to discover the enchanting corners of this New England state, where history, art, and nature converge to create the ideal weekend retreat.