8 Most Breathtaking Towns In Massachusetts

Massachusetts has been a favorite vacation spot for centuries, which is no surprise given its approximately 1,500 miles of rugged and pristine shoreline. In addition to its beach towns, however, you will also find beautiful mountain towns in the west, along with incredible landmarks from the American Revolution. Whether you are planning a weekend by the sea or a trip through the Berkshires, these eight towns will undoubtedly steal your heart and take your breath away.

Concord

Few places in New England have preserved American history, especially from the Revolutionary era, as well as Concord. Many of the town’s buildings date back to the 18th century, filled with stories. One example is the Wright Tavern, built in 1747, which hosted several key figures involved in the fight for independence. Concord’s North Bridge, or Old North Bridge as the locals call it, is another prominent historic site, marking the location of the iconic “shot heard 'round the world” and the start of the Revolutionary War. For a deeper look at Concord’s role in the Revolution and its broader history, travelers can visit the Concord Museum. Highlights include 10,000-year-old artifacts from Indigenous groups, the 1775 lantern that Paul Revere hung in Boston’s Old North Church, and the desk where iconic poet and author Henry David Thoreau wrote Walden.

Provincetown

Located on the northernmost tip of Cape Cod, Provincetown is home to one of the country’s oldest continuous art colonies. Art museums and galleries across town reflect this rich creative heritage, such as the Provincetown Art Association and Museum, which hosts a permanent collection, rotating exhibitions, and lectures from renowned artists throughout the year. Travelers can also stroll down Commercial Street, a gorgeous, art-centered street lined with local galleries. Bowersock Gallery is a great one to visit, displaying sculptures, paintings, ceramics, glass, and more. Afterward, explore the area’s natural beauty at the Cape Cod National Seashore, which features 40 miles of pristine, biodiverse beaches, ponds, marshes, and uplands.

Oak Bluffs

Part of Martha’s Vineyard, Oak Bluffs is beautiful from the moment you step off the ferry. Ocean Park is the first landmark to greet travelers, a seven-acre waterfront green space popular for picnicking in warm weather and seasonal festivals. There are plenty of beaches in the area to check out, such as Town Beach, also referred to as Inkwell Beach. This sandy stretch of paradise has been a beloved spot to gather and sunbathe since the 19th century. Make sure to take a walk by the Gingerbread Houses while in town as well. These pastel-colored homes with wooden trim were built in the 1800s and now feel straight out of a fairy tale, especially on Grand Illumination Night when the houses are decorated with thousands of lanters. The popular event first began in 1869 and continues to this day.

Rockport

Located on the Atlantic coast, Rockport is a seaside town known for its iconic architecture. The town is home to Motif No. 1, a replica of an iconic red fishing shack known as the most painted building in the world. To celebrate this landmark, the town hosts Motif No. 1 Day, an annual festival with painting events, food trucks, and music that takes place each May. Architecture enthusiasts should also visit the Thacher Island Twin Lights at Cape Ann Light station, two identical lighthouses built in 1861 to replace the original 1771 British structures. Halibut Point State Park is another must-visit spot in Rockport. On a clear day, travelers can see both Mount Agamenticus in Maine and the Isles of Shoals, which are off the New Hampshire coast.

Stockbridge

Surrounded by the Berkshire Mountains, Stockbridge is home to a number of gorgeous attractions. Visitors can begin their trip at the Berkshire Botanical Garden, a 24-acre public garden with dozens of distinct garden areas to explore. If you are hoping to spend your afternoon hiking, the Laurel Hill Association maintains three scenic hiking trails in the area, spread across 460 acres. Art lovers will enjoy Stockbridge's many studios and galleries any time of year, but August is a particuarly nice time to plan a visit, as the town hosts their annual Summer Arts & Crafts Show, which features jury-selected artists and artisans exhibiting their work in the downtown district.

Marblehead

Less than an hour's drive from Boston, Marblehead offers a breathtaking weekend escape from the city. Travelers can start off their weekend sunbathing on Devereux Beach, one of the town’s most popular beaches with about 5 1/2 acres of shoreline, picnic tables, pavilions, benches, and popular take-out counter, Neck Run Cafe. Seaside Park is another wonderful place to spend the afternoon, spanning nearly 34 acres and featuring about a half mile of nature trails, as well as tennis courts, a baseball diamond, and a classic grandstand. After a day outdoors, check out one of Marblehead’s local restaurants, such as The Landing, which is located on the Marblehead Harbor and serves seafood and seasonal, globally-inspired cuisine.

Nantucket

Nantucket is located on an island about 30 miles to the south of Cape Cod. It is easy to embrace the town’s maritime spirit aboard a sailing charter, with several agencies offering excursions. Endeavor Sailing is a highly rated option, operated by a captain with over 40 years of sailing experience who built the boat himself. Across the island, travelers can also explore three lighthouses. Great Point Lighthouse is the most powerful light in New England, and is filled with history. It was built in 1986 after the original lighthouse burned down and the second fell over. Downtown, you will find plenty of charming shops, such as The Skinny Dip, a collective boutique that sells clothing, jewelry, and gifts.

Swampscott

Founded as a fishing village in 1629, Swampscott still proudly preserves its fishing heritage today. This history comes to life at the Swampscott Fish House, a National Historic Landmark built in 1896 that still operates today as the oldest fish house in the country. The lobster trap was also invented by a fisherman in Swapscott, and if you want to try some of the town’s seafood today, consider dining at the Dockside Pub. Menu items include New England seafood classics like lobster rolls, fried clams, and chowder. After lunch, take a stroll through Beach Bluff Park, a small seaside spot with walking paths and benches where local residents often gather after a day's work.

Final Thoughts

With so many seaside towns and historic communities, it is hard to go wrong when choosing a vacation destination in Massachusetts. However, these eight towns stand out as some of the most breathtaking, filled with pristine beaches, historic lighthouses, summer arts festivals, and delicious seafood restaurants. Regardless of the place you choose, you are sure to have an unforgettable trip this year in any one of these breathtaking towns.