A row of eclectic stores next to the harbor in Nantucket, Massachusetts. Image credit Mystic Stock Photography via Shutterstock

11 Most Scenic Small Towns in Massachusetts

Massachusetts, officially known as the Commonwealth of Massachusetts, is the most populous state in the New England region of the northeastern United States. It is bordered by the Atlantic Ocean to the east. The state capital and largest city is Boston, which is one of the oldest cities in the United States. It was the site of the first colony in New England, established by the Pilgrims in Plymouth in 1620, and later played a central role in the American Revolution. The state is also home to Harvard University, the oldest institution of higher education in the United States, founded in 1636.

Additionally, Massachusetts is dotted with scenic small towns that offer beautiful landscapes and a glimpse into America's colonial past. These 11 are the most worthwhile to visit.


Late afternoon in downtown Nantucket overlooking a white picket fenced yard with blooming hydrangeas and Easy Street Boat Basin in the distance.
Late afternoon in downtown Nantucket, Massachusetts. Image credit Gretchen Blair Madden via Shutterstock

Nantucket, Massachusetts, is a captivating island town about 30 miles south of Cape Cod. It encompasses a variety of landscapes, including beaches, heathlands, and marshes. Originally inhabited by the Wampanoag people, Nantucket rose to prominence in the 17th and 18th centuries as a whaling hub. The legacy of this era is deeply embedded in the island's architecture, with many of its buildings and lighthouses dating back to the whaling boom.

For those visiting Nantucket, take a trip to Brant Point Light; it has been a guiding light for sailors since its establishment in 1746. Siasconset Beach, known locally as "Sconset Beach," has soft sands and views of the Atlantic, perfect for a relaxing day by the sea or a stroll along its blush-lined paths. Meanwhile, the Whaling Museum is an immersive exploration of Nantucket's whaling era. It has preserved artifacts, detailed exhibits, and a fully assembled sperm whale skeleton.


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

Chatham, Massachusetts, is a seaside town at the southeastern tip of Cape Cod. Known for its beaches, harbors, and historic lighthouses, Chatham's landscape includes barrier beaches, salt marshes, and woodlands. Historically, Chatham has been a maritime center since its settlement by the English in 1664. This town's location also made it a focal point during historical moments, including being a lookout post during World War II to guard against enemy submarines.

The Monomoy National Wildlife Refuge is a must-see in Chatham for wildlife observation, photography, and hiking. This area is a habitat for numerous bird species—a haven for birdwatchers, especially during migration seasons. The Chatham Fish Pier is another highlight. Visitors can watch local fishermen unload their catch of the day and might even sight seals frolicking nearby. Lastly, no visit to Chatham would be complete without stopping by the Chatham Lighthouse and Beach. The lighthouse, an active navigation aid, offers views of the Atlantic Ocean, while the adjacent beach is great for a peaceful walk or simply soaking in the surroundings.

Oak Bluffs

Beautiful colorful gingerbread houses, cottages in Oak Bluffs center, Martha's Vineyard island
Beautiful colorful gingerbread houses, cottages in Oak Bluffs, Martha's Vineyard island.

Oak Bluffs, located on the northeastern shore of Martha's Vineyard in Massachusetts, was originally established as a Methodist camp meeting site in the 19th century. It is now a summer resort characterized by its Victorian "gingerbread" cottages, beaches, and harbors. The town's history is deeply intertwined with the African American heritage of the island. It has been a significant center for African American intellectuals and artists, especially during the Harlem Renaissance.

In Oak Bluffs, the Martha's Vineyard Camp Meeting Association educates visitors on the town's origins with its colorful cottages and the historic Tabernacle at its heart. It hosts community events and religious services. A ride on the Flying Horses Carousel, the oldest platform carousel in the United States, is an experience for all ages. It captures the nostalgia of Oak Bluffs' past. Meanwhile, Ocean Park has green lawns and views of the ocean for picnics, kite flying, or enjoying an afternoon amidst the gentle sea breezes.


Aerial view of Newburyport, Massachusetts, USA.
Overlooking Newburyport, Massachusetts.

Newburyport, Massachusetts, is nestled at the mouth of the Merrimack River near the Atlantic Ocean. Established in 1764, this coastal town flourished as a shipbuilding center and major seaport for international trade, particularly in the Federal period. This left an architectural legacy of preserved Federalist homes and buildings. The city's waterfront played a role in the early American economy and has transformed into a spot for community and cultural events.

Visitors to Newburyport should visit Plum Island, a barrier island just off the coast. It has sandy beaches, dunes, and the Parker River National Wildlife Refuge and is a favorite among birdwatchers, beachgoers, and nature enthusiasts. Additionally, Maudslay State Park has a network of trails through manicured gardens, forests, and along the Merrimack River, ideal for hiking, birding, and seasonal floral displays. Finally, the Custom House Maritime Museum, housed in an 1835 Federal-style building, delves into Newburyport's maritime history, with exhibits on shipbuilding, sea trade, and the US Coast Guard.

Woods Hole

Nobska Lighthouse, Woods Hole, Cape Cod
Nobska Lighthouse, Woods Hole, Cape Cod.

Woods Hole, Massachusetts, is a village located at the southwestern tip of Cape Cod in the town of Falmouth. Its deep natural harbor has made it an important center for oceanic research and ferry transportation to the islands. Woods Hole has been home to a community of fishermen, whalers, and oceanographers since the 19th century. The establishment of several prominent scientific institutions, including the Woods Hole Oceanographic Institution in the early 20th century, solidified its reputation as a place for marine research and education. The Woods Hole Oceanographic Institution educates visitors on ocean science with its exhibits on deep-sea exploration, marine ecosystems, and the institution's research vessels and submersibles.

Nearby, Nobska Light stands as a lighthouse with panoramic views of Vineyard Sound and the Elizabeth Islands. It offers a glimpse into the navigational importance of the area. For a nature walk with coastal vistas, The Knob, a small, rocky promontory extending into Buzzards Bay, has trails leading to secluded beaches and overlooks.


Rockport Harbor aerial view including Bearskin Neck and Motif Number 1 building in historic waterfront village of Rockport, Massachusetts
Bearskin Neck and Motif Number 1 building in historic waterfront village of Rockport, Massachusetts.

Rockport is a coastal town on the Cape Ann peninsula. Geographically, Rockport is blessed with rocky beaches, clear waters, and vistas of the Atlantic Ocean—it is a magnet for photographers. The town has roots in fishing, shipbuilding, and granite quarrying. Over time, Rockport's scenery attracted a vibrant community of artists, transforming it into a flourishing center for the arts by the early 20th century.

In Rockport, Halibut Point State Park is a must-visit. The park's trails meander through a landscape of quarried granite to ocean overlooks, an up-close look at the region's geological history. The Rockport Art Association & Museum, established to foster and celebrate the local artistic community, showcases works by regional artists across a range of mediums. The museum reflects the area's artistic legacy and ongoing inspiration to creatives. And, no visit to Rockport would be complete without seeing Motif Number 1. Situated in the heart of Rockport's historic Bearskin Neck, this red fishing shack is one of the most painted buildings in America.


A cute little Red Tug boat, The Daisy Mae, at a dock or pier on Lewis Bay inlet in Cape Cod, Massachusetts, Near Hyannis Harbor.
A cute little Red Tug boat, The Daisy Mae, at a dock or pier in Cape Cod, Massachusetts, near Hyannis Harbor.

Hyannis, the largest of seven villages in the town of Barnstable, Massachusetts, is the commercial and transportation center of Cape Cod. Geographically, it's located on the southern shore of Cape Cod, with direct access to both Nantucket and Martha's Vineyard via ferry. Hyannis has a waterfront district and is a summer retreat for the Kennedy family. The maritime history is reflected in its architecture, from historic sea captains' homes to the bustling Main Street.

For visitors to Hyannis, the John F. Kennedy Hyannis Museum gives an intimate perspective on the Kennedy family's life and times in Hyannis. The museum's photographs, artifacts, and narratives reveal the connection between the Kennedys and this coastal community. The Cape Cod Melody Tent, one of the oldest continuously operated tent theatres in the United States, is an entertainment experience. A variety of performances, from musical acts to comedy shows, are hosted here within its in-the-round setting. Lastly, Kalmus Beach has excellent wind-surfing conditions due to the steady winds coming off Nantucket Sound. It is a favorite spot for both relaxation and aquatic activities.


Immaculate Conception Church, Mary, Queen of the Apostles Parish on 15 Hawthorne Blvd, Salem, Massachusetts
Immaculate Conception Church, Mary, Queen of the Apostles Parish, Salem, Massachusetts.

Salem, Massachusetts, is a town famously known for the Salem witch trials of 1692. Founded in 1626, this historic town quickly became a center for Puritan activity, maritime trade, and later, the American privateering fleet during the Revolutionary War. The infamous witch trials have cast a long shadow over the town's legacy, but Salem's history is also intertwined with the Age of Sail when it was a wealthy national center for shipbuilding and overseas trade.

Visitors to Salem cannot miss the Salem Witch Museum. It dives into the history of the 1692 witch trials, utilizing life-size figures, lighting, and narration to bring the stories of accused witches and their accusers to life. The House of the Seven Gables, made famous by Nathaniel Hawthorne’s novel, not only explores the literary significance of Hawthorne’s work but also allows visitors to experience 17th-century architecture and learn about the house's role in Salem's maritime activities. Lastly, the Salem Maritime National Historic Site, the first National Historic Site established in the United States, encompasses a waterfront area that includes historic buildings, wharves, and the reconstructed tall ship Friendship of Salem.


The landmark Dexter Grist Mill and Water Wheel in Sandwich, Massachusetts.
The landmark Dexter Grist Mill and Water Wheel in Sandwich, Massachusetts.

Sandwich, established in 1637, is the oldest town on Cape Cod. Geographically, Sandwich is along the Cape Cod Bay at the eastern end of the Cape Cod Canal and has a mix of coastal landscapes, marshes, and wooded areas. This town was part of the early Plymouth Colony and played a role in the American glass industry during the 19th century. The town's architecture, including numerous well-preserved colonial homes, churches, and the Dexter Grist Mill, reflects its long and varied history.

For visitors eager to explore Sandwich's nature, Heritage Museums & Gardens houses gardens, a restored antique carousel, and a collection of American folk art. It embodies the spirit of American innovation and design. The Sandwich Glass Museum illuminates the town's contribution to the American glass industry with live glassblowing demonstrations and antique glass collections. Another top attraction is the Green Briar Nature Center and Jam Kitchen. It invites guests to explore walking trails, enjoy educational programs about local flora and fauna, and experience the tradition of jam-making.


Aerial view of Edgartown, Massachusetts
Overlooking Edgartown, Massachusetts.

Edgartown is on the eastern shore of Martha's Vineyard, known for its Greek Revival homes and beaches. As the island's first colonial settlement, founded in 1642, Edgartown grew to prominence in the 18th and 19th centuries as a whaling hotspot, with its prosperity reflected in the grand homes and buildings that line its streets. The town's harbor, once teeming with whaling ships, now welcomes yachts and fishing boats.

The Martha's Vineyard Museum, recently relocated and expanded, provides insights into the island's maritime heritage and Indigenous cultures. A short ferry ride to Chappaquiddick Island is an escape to a quieter part of Martha's Vineyard, with unspoiled natural landscapes, the historic Cape Poge Lighthouse, and stretches of beaches. Meanwhile, the Felix Neck Wildlife Sanctuary has miles of trails through meadows, woodlands, and salt marshes, along with opportunities for bird watching, guided kayak tours, and educational programs about the local ecosystem.


Marina in Manchester-by-the-Sea, Massachusetts.
Marina in Manchester-by-the-Sea, Massachusetts.

Manchester-by-the-Sea is a New England coastal town located on Cape Ann, north of Boston. The town dates back to its settlement in 1629. Initially known simply as Manchester, the "by-the-Sea" suffix was officially adopted in the 19th century to distinguish it from other Manchesters. The town's geography includes beaches, rocky shorelines, and forests. Manchester-by-the-Sea used to be a place for shipbuilding and fishing. It has transformed into a summer retreat for Boston's elite, with grand estates and mansions dotting its landscape.

Singing Beach is one of the town's most beloved natural attractions, famous for the unique "singing" sound the sand makes when walked upon. Its views and clear waters make it the spot for a day of relaxation and swimming. Nature enthusiasts will find Agassiz Rock a fascinating destination, where glacial action has created granite formations and a forest setting for hiking. The Manchester Historical Museum, housed in the 18th-century Trask House, houses artifacts, photographs, and exhibits that tell the story of the town's maritime heritage.

The scenic small towns in Massachusetts blend the old with the new, gifting visitors who travel to them natural and architectural beauty. Towns like Nantucket and Sandwich serve as prime examples, where the essence of New England's colonial past and natural splendor is palpable in every street, beach, and historical edifice. These locales, among others, underscore Massachusetts' multifaceted identity. It is the charm and tranquility of the state's small towns that enrich its narrative.

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