The Most Picturesque Towns In Massachusetts
In Massachusetts, endearing small towns take center stage, offering seamless connections to nature across immaculate landscapes. The state is full of magical sights, spanning centuries of cultural and historical landmarks from its fascinating past, and it goes hand in hand with sightseeing alongside stunning capes, sandy beaches, and historic harborfronts, or the Berkshires' lush, secluded trails.
From Salem's grand mansions to Edgartown's affluent island vibes, you can take a road trip down Cape Cod, stopping at some of the state's most picturesque towns along the way. The Atlantic Ocean and colonial-era architecture frame your Instagrammable journey, with fresh air, views easy on the eyes for photography and relaxation, gallery crawls, dining, and shopping, like Rockport's Motif 1 and Bearskin Neck.
Chatham
Chatham embraces you midway along this sweeping curve, with enchanting sites like the Godfrey Windmill (1797) and the mysterious Monomoy Island offshore in the open ocean. The sun rises over the Atlantic, ideal for an early morning paddle before the large sandy beach steals your afternoon alongside a local seal colony and the Chatham Light, erected as a pair in 1808, whose double was moved elsewhere in 1923.
The town at the heart of Cape Cod is ideal for an art crawl among galleries and historic homes like the 1752 home that houses the Atwood Museum, while the railroad museum occupies a circa-1887 train station. Grab a walking-trail map at the Monomoy National Wildlife Refuge for a nature hike, then catch a flick at the pastel Orpheum Theater (c. 1916) with intricate features and a vintage feel. The pair of pristine beaches along the western edge of town offers a magical vantage point for sunset-watching.
Concord
While the Bay State offers over 1,500 miles of ocean coast, gems dotting the picturesque heartland beckon you off the beaten path, like the historic town of Concord at the tri-river intersection in the wetlands of Great Meadows National Wildlife Refuge, with birds and wildlife and hiking access via the Reformatory Branch Trail. Meanwhile, bikers find the paved Bruce Freeman Rail Trail ideal for fall foliage peeping along an old railway directly through Concord, connecting other small towns.
The long-distance Bay Circuit Trail winds around the local Walden Pond, where Henry David Thoreau wrote his book Walden, making it a literal hotspot in the summer for swimming and paddling in your canoe, kayak, or paddleboard, with rentals from South Bridge Boat House, which can take you cruising down Concord's rivers. Finally, Louisa May Alcott's Orchard House (c. 1650) invites you in for a tour and events of her heirloom-filled hom,e where she wrote and set "Little Women" in 1868.
Edgartown
Just seven miles off the Cape Cod coast, Edgartown frames your stress-free escape in open ocean vistas and Martha’s Vineyard's natural beauty. The seaport village on the eastern side of the island is one of the state's most alluring destinations, blending retro charm and modern amenities, with New England staples like stately homes and historic inns, a classic New England lighthouse, and beaches, like the 2-mile sandy stretch, to sprawl along and play in the shallows on the set for the film "Jaws."
Whether it's a romantic trip or a friends’ getaway, indulge in island time alongside historic architecture, boutique shopping, and locally sourced cuisine, with annual events like Pink & Green Weekend and a Mother's Day festival in May, both spotlighting the town's pink hydrangeas and green spaces. Just east, sprawling refuges encompass sandy shores, secluded trails, and wildlife, and Mytoi Japanese Garden offers serene walking paths, a pond, traditional Japanese structures, and seasonal flowers.
Newburyport
Boasting a vibrant harborfront on the Merrimack River, this historic port town between Salem and Portsmouth, NH, in northeastern Massachusetts, is ideal for a weekend trip to really imbibe the 18th-century vibes. Once a major maritime trading center, travelers enjoy Newburyport's extraordinary collection of federal architecture, waterfront parks, dining, and the harborside boardwalk from the marina to the museum artifacts and ship models, tracing back to its glory days inside an 1835 building.
Since a catastrophic fire in 1811 leveled downtown, you can explore the history behind the brick facades through the restaurants, trendy boutiques, and art galleries around Market Square. Hop to the oceanfront for a beach day on Plum Island, under the watchful eye of the Plum Island Lighthouse, with seasonal tours and scenic views. Minutes inland, Maudslay State Park covers an old estate with horticulture to explore and relax amid floral diversity, spectacular trees, and mountain laurel stands.
Provincetown
Served by two seasonal ferries from Boston and one from Plymouth, this Cape Cod gem north of Chatham is not forgotten off the beaten path. Framed by the sky, sea, and sand, P-town is frequently praised as one of the state's top destinations at the very tip of the sandy curve. Whether you're after a gallery crawl or to enthrall your taste buds, expect a colorful array of personalities to keep you company along the harborfront, including the LGBTQ community, beach lovers, and creatives alike.
Settled for centuries by Native Americans and explorers, the Pilgrims first landed here in the New World in 1620, on the spot marked by the 252-foot Pilgrim Monument, the US's tallest granite structure. Having sheltered fishermen, whalers, and artists drawn by the unique light and landscape, Charles Hawthorne opened the Cape Cod School of Art in 1899, solidifying P-town as America’s oldest continuous art colony. Also, whale-watching excursions began here by the Center for Coastal Studies.
Rockport
Rockport single-handedly encapsulates the New England charm just an hour from Boston. Having inspired many artists, such as Winslow Homer, you can discover a unique history entwined in one of America's oldest art colonies and the seafood industry, with over 30 galleries, the Rockport Art Association & Museum, and exquisite fresh-from-sea dining. Home to Motif 1, a replica of the original 1840 fishing shack, this colorful structure is a local gem featured on travel covers.
Grab a coffee from Bean & Leaf Cafe for a stroll along the harbor to the Front Beach, with amenities, seaglass, and nearby eateries. Bearskin Neck juts into Rockport Harbor with quaint little studios and shops for eclectic shopping, engulfed in sea views. From the granite pier and miles of sandy beaches to the Straitsmouth Island Light Station with opinions from the Seafarer Inn, there's much to explore until the uncommonly magical light catches the water in the coves, creating a truly romantic getaway.
Salem
This cultural mecca north of Boston is known as much for its retail and gastronomical endeavors as for its history of witches, pirates, sea captains, and literature. Home to under 50,000, Salem has a chill, urban vibe and a fantastic, walkable downtown, spanning four centuries of architecture, from the grand mansions on Chestnut Street to the Victorian cottages near the Salem Common. The Ropes Mansion Garden has a free, beautiful, and quiet garden in the back of an 18th-century Georgian Colonial.
The House of the Seven Gables offers verdant seaside gardens and seasonal tours of the 1668 home that inspired Hawthorne's novel across from his birthplace. Beyond its enigmatic mansions and museums, historic charm blends seamlessly with ocean views, from Willows Park's seaside promenade for strolls and picnics to the secluded Winter Island Park, with tent and RV camping sites for days in sweeping ocean vistas by Waikiki Beach, a historic lighthouse, and a public boat launch.
Sandwich
Founded in 1637 and known for producing distinctive glassware in the 1800s, Cape Cod's oldest town is an ideal weekend by the beach along a wide sandy swath with grassy dunes and rentable cottages. As one of the first stops along Cape Cod on the historic Route 6A, with broad marshes bordering the sea, you can explore two different sides of this town, along the Sandwich Boardwalk and the Town Hall Square, featuring over 200 buildings alone to power through, ringed by ancient shade trees.
Walking past galleries, potters, and glassblowers, you can view an impressive glassblowing collection and demos at the local museum, snap a selfie by the 1847 First Church's soaring steeple, and buy souvenirs and home decor. The 1654 mill grinds corn nearby on tranquil Shawme Pond, with more weathered clapboard and Greek Revival homes. Just off the historic route, the Heritage Museums & Gardens offers wooded trails, exquisite gardens and sculptures, plus a vintage automobile museum.
In the small Bay State, it is not hard to find scenic pleasures and New England charm, with quick access from Boston and states like New Hampshire. Concord is a "literal" hotspot with past locals like Louisa May Alcott and Henry David Thoreau, where they wrote their classics.
Massachusetts is a state of firsts, including the first public park in the US, established in 1634 in the Bay State, where Dunkin' Donuts first opened shop. Provincetown, the nation's first art colony, is a premier destination for whale watching.
