Massachusetts, steeped in early American history, is dotted with towns that preserve the essence of colonial times. These charming destinations offer a glimpse into the past with their well-preserved architecture, storied streets, and rich cultural heritage. Join us as we count down the 19 most enchanting colonial towns in the Bay State, revealing hidden gems and timeless tales along the way.
19. Provincetown: A Colonial Town at Land’s End
Nestled at the tip of Cape Cod, Provincetown is where the Pilgrims first touched land before settling in Plymouth. This vibrant town boasts a lively arts scene and a welcoming atmosphere. Wander through its narrow streets lined with historic homes, and don’t miss the Pilgrim Monument—a tribute to the Mayflower’s arrival. A hidden gem is the serene Beech Forest, perfect for a tranquil walk away from the bustling harbor. With an average price of $1,600,000, a 3-4 bedroom home in Provincetown offers a blend of coastal charm and historic allure.
18. Waltham: The Watch City with Colonial Charm
While Waltham is known for its role in the Industrial Revolution, it also harbors colonial charm. Visit the Gore Place, a 50-acre estate featuring a magnificent Federal-period mansion that offers a window into early 19th-century life. The city’s historic district along Moody Street blends old and new, with preserved buildings housing modern eateries and shops. The Charles River Museum of Industry and Innovation, located in an old textile mill, adds to Waltham’s unique blend of history. In Waltham, 3-4 bedroom homes average $740,018, making it a desirable choice for those seeking history with affordability.
17. Amherst: A Colonial Town with Literary Legacy
Amherst combines colonial heritage with a rich literary tradition. The well-preserved Emily Dickinson Museum offers insights into the poet’s life and times. Stroll through the town center to admire colonial-era buildings intermingled with cozy cafes and bookstores. A lesser-known treasure is the Amherst History Museum, housed in the 1750 Simeon Strong House, showcasing artifacts that chronicle the town’s storied past. The average price for a 3-4 bedroom home in Amherst is $500,000, providing a literary retreat at an accessible cost.
16. Gloucester: America’s Oldest Seaport
Established in 1623, Gloucester claims the title of America’s oldest seaport. Its colonial history is etched into the rugged coastline and picturesque harbor. The Maritime Gloucester museum delves into the town’s seafaring legacy. For a hidden gem, hike up to the Dogtown Commons, an abandoned colonial settlement now a woodland area adorned with mysterious Babson boulders inscribed with inspirational sayings. With an average price of $654,900 for a 3-4 bedroom home, Gloucester offers coastal living steeped in history.
15. Cambridge: Colonial Roots Amidst Academic Prestige
Cambridge is renowned for Harvard and MIT, but its colonial roots run deep. The Longfellow House–Washington’s Headquarters National Historic Site served as George Washington’s base during the Siege of Boston. Explore the charming Brattle Street, known as “Tory Row,” lined with grand colonial mansions. For a quiet retreat, visit the historic Mount Auburn Cemetery, America’s first garden cemetery, offering peaceful paths and remarkable monuments. Homes with 3-4 bedrooms in Cambridge average $1,870,000, reflecting the area’s prestigious and historic appeal.
14. Hingham: The Lexington of the Sea
Hingham, settled in 1633, boasts a wealth of colonial architecture along its scenic waterfront. The Old Ship Church, built in 1681, is the oldest continuously used wooden church in North America. Stroll down Main Street to admire the beautifully preserved homes. A hidden delight is World’s End, a 251-acre park with walking trails and sweeping views of the Boston skyline, offering a glimpse of Hingham’s natural beauty. A 3-4 bedroom home in Hingham averages $1,250,000, a reflection of its historic charm and seaside location.
13. Sudbury: Historic Inns and Rural Beauty
Sudbury captures the rustic charm of colonial Massachusetts. Visit the Wayside Inn, made famous by Henry Wadsworth Longfellow’s “Tales of a Wayside Inn,” which is the oldest operating inn in the country. The town’s rolling hills and preserved landscapes provide a peaceful backdrop. Don’t miss the Martha Mary Chapel and the Grist Mill on the inn’s property—both picturesque spots that transport you back in time. In Sudbury, 3-4 bedroom homes average $1,150,000, offering a serene escape steeped in history.
12. Edgartown: Elegant Whaling Port on Martha’s Vineyard
Edgartown on Martha’s Vineyard exudes elegance with its stately Greek Revival homes built by prosperous whaling captains. The Old Whaling Church stands as a testament to this affluent past. Meander through the shaded streets adorned with manicured gardens. For a hidden gem, hop on the Chappy Ferry to Chappaquiddick Island and explore the Mytoi Japanese Garden—a tranquil oasis of exotic and native plants. With an average price of $1,884,071 for a 3-4 bedroom home, Edgartown offers an exclusive blend of elegance and coastal beauty.
11. Nantucket: An Island Frozen in Time
Once the whaling capital of the world, Nantucket Island offers cobblestone streets and weathered gray-shingled homes that preserve its colonial-era charm. The Nantucket Whaling Museum provides fascinating insights into this bygone industry. Venture to the lesser-known Old Mill, the oldest functioning windmill in the country, for panoramic views of the island. Sunset at Madaket Beach is a local favorite, showcasing Nantucket’s natural beauty. A 3-4 bedroom home on Nantucket averages $2,574,570, reflecting the island’s exclusivity and timeless appeal.
10. Rockport: An Artistic Coastal Retreat
Rockport, with its iconic Motif Number 1 fishing shack, has long attracted artists to its scenic shores. The town’s colonial heritage is evident in its quaint cottages and historic districts. Bearskin Neck, a narrow peninsula dotted with shops and galleries, invites leisurely exploration. A hidden treasure is the Paper House, a unique museum entirely constructed from newspaper—a testament to Rockport’s quirky charm. The average price of a 3-4 bedroom home in Rockport is $785,000, offering a charming coastal lifestyle with artistic flair.
9. Lexington: The Cradle of American Liberty
Lexington holds a pivotal place in American history as the site of the first battle of the Revolutionary War. Visit the Battle Green where the “shot heard ’round the world” was fired. The Hancock-Clarke House and Buckman Tavern offer glimpses into colonial life. For a peaceful walk, explore the Minute Man National Historical Park’s trails that weave through historic landscapes and landmarks. With an average price of $1,595,000 for a 3-4 bedroom home, Lexington combines historical significance with modern-day prestige.
8. Stockbridge: A Town Straight Out of a Painting
Nestled in the Berkshires, Stockbridge seems frozen in time, capturing the quintessential New England village portrayed in Norman Rockwell’s artwork. The Red Lion Inn, dating back to 1773, welcomes visitors with its antique charm. The Norman Rockwell Museum houses an extensive collection of the artist’s works. Nearby, the Mission House provides insights into early missionary life among Native Americans—a slice of colonial history often overlooked. Homes with 3-4 bedrooms in Stockbridge average $600,000, making it an idyllic and affordable New England retreat.
7. Ipswich: Home to America’s First Period Houses
Ipswich boasts the largest concentration of First Period (1625-1725) homes in the country. The John Whipple House and the Heard-Lakeman House are prime examples of early American architecture. Along the scenic Ipswich River, you’ll find the serene Willowdale State Forest. A local secret is Crane Beach, offering pristine sands and dunes—a perfect spot to unwind while appreciating the town’s natural splendor. In Ipswich, a 3-4 bedroom home averages $740,000, blending historical charm with coastal living.
6. Newburyport: A Maritime Gem
With its beautifully preserved Federalist architecture, Newburyport reflects its prosperous maritime past. The Custom House Maritime Museum sheds light on the town’s shipbuilding and trading history. Stroll along the waterfront boardwalk for picturesque views. For a unique experience, explore Maudslay State Park, a former estate with gardens, meadows, and hidden ruins amidst towering pines. The average price of a 3-4 bedroom home in Newburyport is $950,000, offering a balance of historic charm and waterfront beauty.
5. Deerfield: A Living History Museum
Deerfield is a remarkable enclave of 18th-century homes, meticulously preserved along its mile-long main street. Historic Deerfield offers immersive experiences, with costumed interpreters bringing colonial history to life. Visit the Memorial Hall Museum, one of the oldest museums in New England, housing an eclectic collection of artifacts. The Indian House Memorial Children’s Museum is a hidden gem, engaging young minds with hands-on exhibits. With an average price of $400,000 for a 3-4 bedroom home, Deerfield provides a historically rich yet affordable option.
Marblehead’s narrow, winding streets are lined with colorful colonial homes overlooking a picturesque harbor. Fort Sewall, a coastal fortification dating back to 1644, offers panoramic ocean views. Discover the lesser-known Gingerbread Hill, a quaint area with charming cottages and gardens. Marblehead’s rich maritime heritage and stunning coastal scenery make it a true colonial treasure. A 3-4 bedroom home in Marblehead averages $935,000, reflecting its blend of seaside elegance and historic significance.
3. Plymouth: The Landing Place of the Pilgrims
Plymouth holds a special place in American lore as the Pilgrims’ landing site in 1620. Visit Plymouth Rock and the Mayflower II, a replica of the original ship. Plimoth Patuxet Museums provide a re-created 17th-century English village and Wampanoag Homesite. For a hidden gem, explore the lesser-known Burial Hill, an ancient cemetery offering panoramic views and a connection to the town’s earliest settlers. Homes with 3-4 bedrooms in Plymouth average $575,000, making it a historic yet affordable destination.
2. Salem: A Seaport with a Mysterious Past
Famous for its 1692 witch trials, Salem’s rich history extends beyond this dark chapter. The city’s colonial architecture, including the House of the Seven Gables, inspired by Nathaniel Hawthorne’s novel, captivates visitors. The Salem Maritime National Historic Site highlights its significance as a booming seaport. Venture to Proctor’s Ledge, recently identified as the execution site of the accused witches—a sobering and lesser-known historical spot. With an average price of $611,000 for a 3-4 bedroom home, Salem blends historic intrigue with coastal living.
1. Concord: Where Revolutionary History Lives
Concord embodies the spirit of early America, from the first battles of the Revolution to the transcendentalist movement. Visit the Old North Bridge, site of “the shot heard ’round the world,” and the Minute Man National Historical Park. Literary enthusiasts will appreciate Walden Pond, where Henry David Thoreau penned his reflections. The Sleepy Hollow Cemetery, final resting place of Emerson, Hawthorne, and Alcott, offers a peaceful and reflective hidden gem. In Concord, the average price for a 3-4 bedroom home is $1,450,000, reflecting its blend of historical prominence and natural beauty.
