A young family walks through the charming Cape Cod town of Chatham, Massachusetts. Image credit James Kirkikis via Shutterstock

12 Best Towns in Massachusetts to Visit in 2024

Massachusetts sits in the Northeastern region of the United States of America and is cornered by the Gulf of Maine and the Atlantic Ocean. Esteemed as one of the best states to live in 2022 and 2023, Massachusetts is a colorful, hospitable, and economically vibrant state.

Home to tourist landmarks, sports centers, and art centers, Massachusetts is well-replete with charming towns that will help you relish your holidays. While there are many popular towns and the big city of Boston along the coast, some of the best towns in Massachusetts are hidden throughout the state, and the aesthetic appeal of each town will wow you in 2024.


Houses in Stockbridge, Massachusetts, USA.
Houses in Stockbridge, Massachusetts. By Joe Mabel, CC BY-SA 3.0, Wikimedia Commons

Stockbridge is a fascinating town in the Berkshires of Western Massachusetts, popular for its quaint Main Street and rich cultural heritage. Nearby Lenox is famous for being the summer home of the Boston Symphony Orchestra.

The Stockbridge Library, Museum, and Archives, as well as the Berkshire Museum, 22 minutes away, showcase the town's history and art. The Naumkeag Museum also serves as a historic estate with a mansion and gardens, giving visitors a more intimate feeling of the town.

The Tanglewood Music Festival, held between June and September, is a chance to enjoy the town's music and art performances. The Stockbridge Inn is one of the best bed and breakfasts in the town, where you can relax and feel the town's aura.


Historic commercial buildings on Main Street in downtown Gloucester, Massachusetts, via Wangkun Jia / Shutterstock.com
Historic commercial buildings on Main Street in downtown Gloucester, Massachusetts. Image credit Wangkun Jia via Shutterstock.com

Gloucester is a historic fishing port on the North Shore of Massachusetts, known for its stunning coastline and the historic Eastern Point Lighthouse. Once a major center for the granite industry, Gloucester has now evolved to become a bubbling center for sailing and seafood.

The Cape Ann Museum is a great place to begin your adventure for a glimpse into the town's history. You may also want to visit the Hammond Castle Museum, a medieval-style castle built by inventor John Hays Hammond Jr. To enjoy the beauty of the town's natural environment, the Gloucester Harbor Walk is a scenic walking trail for everyone to enjoy.

The Hotel at Cape Ann Marina, with its waterfront view, is the perfect resort for visitors. You can also choose to attend the Gloucester Waterfront Festival, held every August with family, friends, and locals.


The Witch House. Salem, Massachusetts, USA.
The Witch House, Salem, Massachusetts.

Sitting on the North Shore of Massachusetts is a historic town known for its infamous witch trials and maritime heritage. Salem is very famous for its Halloween celebrations, historic homes, and witchcraft-related tourism which is occasionally a source of debate.

A visit to The House of the Seven Gables is a proper way to start your tour. This historic mansion was made famous by Nathaniel Hawthorne's novel. The Salem Witch Museum and Peabody Essex Museum showcase the town's witch trial history and art, respectively. You might also like a meal at Rockafellas Restaurant or Brothers Taverna.


Stage Harbor at Chatham, Massachusetts in Cape Cod.
Stage Harbor at Chatham, Massachusetts in Cape Cod.

Founded in 1665 and famous for its fishing industry and summer tourism, Chatham is a charming coastal town on the elbow of Cape Cod blessed with beautiful beaches and picturesque lighthouses.

Beginning at the Chatham Lighthouse, a historic lighthouse with stunning views of the Atlantic, visitors can embrace the town's spectacular nature and the dynamic wildlife ecosystem protected in the Monomoy National Wildlife Refuge.

The Chatham Bars Inn is a historic place of comfort for tourists. The Chatham Oktoberfest, a German-themed festival held in October, and the Chatham Summer Festival, held in July, are wonderful times of celebration for the locals.


View of buildings in downtown Northampton, Massachusetts.
Downtown Northampton, Massachusetts. Image credit EQRoy via Shutterstock.com

Northampton is a vibrant college town in the Pioneer Valley of western Massachusetts. Once a giant in the silk industry, Northampton is now famous for its historic architecture, outlandish beauty, and tourist attractions.

It is home to Smith College, which houses the Smith College Museum of Art, where you can see art from different parts of the world. Thornes Marketplace and the Northampton district are historic areas around the city that are perfect for visits and making good travel memories.

Enjoy the entertainment scene at the Northampton Jazz Festival, held every September, to celebrate jazz music and the town's rich culture.


Crowds of people on Commercial Street in Provincetown, Massachusetts.
Crowds of people on Commercial Street in Provincetown, Massachusetts. Image credit Mystic Stock Photography via Shutterstock.com

Provincetown is a picturesque coastal town at the tip of Cape Cod famous for its stunning beaches, artistic community, and rich maritime history.

You might like to check out the nearby Cape Cod National Seashore, where you can enjoy the scenic view of the overlooking landscape while hiking or biking. The history of the town is well preserved in the Provincetown Art Association and Museum. The Crown and Anchor Inn and the Provincetown Inn are some of the best accommodations in town.


Storefronts in historic Concord, Massachusetts.
Storefronts in historic Concord, Massachusetts. Image credit Joseph Sohm via Shutterstock

Famous for being the birthplace of the American Revolution, Concord has become a remarkable town in Eastern Massachusetts. The first shot of the Revolutionary War was recorded in Concord at The Old North Bridge.

Concord is famous for its literary heritage, and you can find glimpses in the Concord Museum.

For outdoor enthusiasts, Concord offers the Walden Pond State Reservation, and you can also enjoy the ambiance of the Concord's Colonial Inn. The Concord Festival of Authors in October is great for getting insights about literature and writing.


Late afternoon in downtown Nantucket, Massachusetts.
Late afternoon in downtown Nantucket, Massachusetts. Image credit Gretchen Blair Madden via Shutterstock

Nantucket is famous for its summer tourism and whaling heritage. It is the choicest holiday destination for lovers of the sea and outdoors. It is a scenic island town off the coast of Cape Cod, and its beautiful beaches attract tourists from all over the world.

The island's history is preserved in the Whaling Museum, where exhibits of its whaling history are displayed. If you are a history buff, the Great Point Lighthouse will immediately catch your eye.

The Nantucket Inn and Life House are great accommodations with beautiful views of the island. On a good day, you should also check out Cisco Beach.

The town hosts the Nantucket Film Festival and Christmas Stroll in June and December, respectively, with vibrant music and cultural displays.


Historic timber building housing the Historic Deerfield Museum Gift Shop and Bookstore in Deerfield, Massachusetts.
Historic Deerfield Museum Gift Shop and Bookstore in Deerfield, Massachusetts. Image credit Alizada Studios via Shutterstock.com

Deerfield is a historic town in western Massachusetts famous for its colonial architecture and cultural scene. Featuring as one of the best towns in Massachusetts, its historic district and museum, Historic Deerfield, Memorial Hall Museum, and Magic Wings Butterfly Conservatory are some of the best attractions in the town.

The Flynt Center of Early New England Life showcases the region's history and culture.

You might enjoy a stroll or bike ride along the scenic Connecticut River Greenway with loved ones. The Deerfield Inn is a comfortable spot for visitors to lodge and enjoy the hospitality of the locals.


Scenic view of Main Street of the historic town of Hudson, Massachusetts.
Scenic view of Main Street of the historic town of Hudson, Massachusetts. Image credit Yingna Cai via Shutterstock.com

If there is one town with something for everyone, it is Hudson. Located in central Massachusetts and known for its historic architecture and food, Hudson is a hotspot for visitors.

Welcoming thousands of visitors yearly, the American Heritage Museum and its historic district with idyllic buildings are constantly visited and photographed by those enjoying the moment. The Assabet River Rail Trail, which runs through five towns, including Hudson, leaves you wanting more outdoor adventures with its breathtaking views and serenity.

The Hudson Recreation Department has something for the whole family, and a visit to Lake Boon will leave you in awe of nature for a long time. For a feel of the town's entertainment scene, be sure to attend the Hudson Festival in June.


Aerial view of the historic town center of Wayland, Massachusetts.
Overlooking the historic town center of Wayland, Massachusetts.

Wayland is a lovely town in eastern Massachusetts. It is famous for the beautiful parks that abound throughout the town. The town has a very modest population and a charming aura as well.

Wayland Town Beach and Dudley Pond on Lake Cochituate are beautiful wonders of nature around here. Great Meadows National Wildlife Refuge, 4.5 miles from the town, offers another thrilling experience during your stay. The Wayland Historical Society offers a glimpse into the town's history.


Crosby Lane Beach, Brewster, Massachusetts (Cape Cod).
Crosby Lane Beach, Brewster, Massachusetts (Cape Cod).

Joining the other towns in Cape Cod is Brewster, known for its beautiful beaches and historic architecture. Its beachfront hums exciting tunes that many tourists enjoy throughout the summer, adding to its huge aesthetic appeal.

Upon visiting Brewster, you have to visit one of its many beaches. There are quite a number of beaches in town or 10 to 14 minutes away, such as Skaket Beach, Mayflower Beach, Crosby Landing Beach, and Breakwater Beach. Brewster Historic District, with its preserved buildings and walking tours, is a good place to enjoy the town's history.

Visit these twelve towns in 2024, and you will see that Massachusetts is a pleasant, inclusive state. Whether you are a writer, artist, researcher, or just someone looking to unwind, there is so much to enjoy. From beaches to historic buildings and museums, it is time to pack your bags, get on a flight, and enjoy a much-needed vacation.

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