8 Fairy-Tale Small Towns In Massachusetts

The Gingerbread Cottages of Oak Bluffs began as canvas tents pitched for Methodist revival meetings in the 1830s, and the whole village still circles the open-air Tabernacle where those meetings were once held. That layering of unique American history and aesthetic appeal runs through a handful of Massachusetts towns where the streets, the estates, and the natural landscape are as pretty as a picture. Some sit out on Martha's Vineyard and Cape Cod, others deep in the Berkshire hills, and each keeps a scene worth writing home about. Here are eight Massachusetts towns straight out of a fairy tale.

Oak Bluffs

Oak Bluffs on Martha's Vineyard grew out of a 19th-century Methodist campground, and the bones of that camp are still here. Around the Tabernacle sits Wesleyan Grove, more than 300 Carpenter Gothic cottages painted in bold colors, trimmed with scrollwork, and set under Gothic arch windows, which is how the neighborhood earned its Gingerbread name.

Near the wharf, the Martha's Vineyard Flying Horses Carousel has been turning since it arrived from Coney Island in 1884, making it the oldest operating platform carousel in the country. Riders still reach for the brass ring on the way past, and catching it wins a free spin. Circuit Avenue runs through the center with its boutiques, ice cream parlors, and seafood counters, and a few steps from downtown is Inkwell Beach, a historic gathering place for the island's Black community and a stop on the African American Heritage Trail.

Stockbridge

Norman Rockwell spent the last 25 years of his life in Stockbridge, and Main Street here is the one he painted, gas lamps and all. The Red Lion Inn has anchored the same corner since 1773, when it opened as a stagecoach stop. Williams & Sons Country Store, in business on Main Street since 1795, still sells penny candy, local soaps, and handmade goods from its narrow rooms.

A short way out of the center, Naumkeag is a 44-room Gilded Age "cottage" whose grounds hold the terraced Blue Steps, a Chinese pagoda, and gardens that step down the hillside. Nearby Chesterwood was the summer home and studio of Daniel Chester French, who carved the seated Lincoln for the Lincoln Memorial, and his working studio still stands on the 122-acre property.

Concord

Concord reads like a literature syllabus laid out along white-steepled streets. Louisa May Alcott wrote and set Little Women at Orchard House in 1868, and the farmhouse, built around 1650, still holds the small desk her father made for her. A walk away, the Old North Bridge stands inside Minute Man National Historical Park, the spot where the 1775 skirmish that opened the Revolution earned its name as "the shot heard 'round the world." The bridge sits over a quiet stretch of the Concord River lined with willows.

Up on Author's Ridge in Sleepy Hollow Cemetery, Henry David Thoreau, Nathaniel Hawthorne, and Ralph Waldo Emerson are buried within a short walk of one another, and a self-guided path connects the graves. Concord's Colonial Inn, whose oldest section dates to 1716 and served as a storehouse for the town's arms in the Revolution, still takes guests and serves New England fare on Monument Square.

Shelburne Falls

The signature sight in Shelburne Falls is a 400-foot former trolley bridge that volunteers replanted as the Bridge of Flowers, and by midsummer, it disappears under blossoms and vines above the Deerfield River. Below, Bridge Street runs past independently owned shops and Baker Pharmacy, a village fixture since the mid-1800s that still pours from a working soda fountain.

At the base of Salmon Falls sit the Glacial Potholes, more than 50 rounded basins that river water and whirling stones drilled into the bedrock after glacial Lake Hitchcock drained roughly 14,000 years ago. It is one of the largest such concentrations anywhere, and the site of the largest pothole on record. The Shelburne Falls Trolley Museum runs its 1896 Trolley Car No. 10 on a short stretch of track, and Salmon Falls Gallery, owned by glassblower Josh Simpson, fills a former grain building with his work and that of dozens of regional artists.

Edgartown

Edgartown made its money from whaling, and the captains built their houses to show it: white clapboard, widow's walks, and deep porches facing the water. Their homes now hold the boutiques along Main Street, and Ben & Bill's Chocolate Emporium anchors the walk near the harbor. The Old Whaling Church, an 1843 Greek Revival built by those same captains, carries six massive columns and a 92-foot clock tower, with hand-painted trompe l'oeil covering the walls inside.

A short ferry ride across to Chappaquiddick reaches Mytoi, a 14-acre Japanese garden of winding paths, azaleas, dwarf maples, and a koi-and-turtle pond on Dike Road. Back on North Water Street, the 1828 Edgartown Lighthouse and the wraparound porches of the Harbor View Hotel close out the town's maritime edge.

Chatham

Chatham holds down the elbow of Cape Cod, where the shoreline breaks into cliffs, dunes, and shingled houses weathered gray by salt air. Main Street carries the shops, among them Yankee Ingenuity, a gallery and gift store open since 1971 and known for its crooked rooftop sign. At Chase Park stands the Godfrey Windmill, a working 1797 grist mill set among trimmed gardens.

Out past Morris Island, the Monomoy National Wildlife Refuge opens miles of trails through pine and salt marsh, and its beaches and flats draw migratory birds and hauled-out seals. For a quieter stop, the Chatham Labyrinth traces a circular walking path near the water, laid out for slow, meditative loops.

Lenox

Lenox fills up every summer for Tanglewood, the Berkshire home of the Boston Symphony Orchestra, but its Gilded Age houses are the year-round draw. Ventfort Hall, completed in 1893 for Sarah Morgan, sister of J.P. Morgan, is a 28,000-square-foot brick mansion whose restoration visitors can walk through room by room. Down the road, The Mount is the house and gardens Edith Wharton designed for herself in 1902, with statuary set among terraces and reflecting pools; she wrote Ethan Frome and The House of Mirth during her years here.

Kennedy Park spreads 500 acres of wooded trails at the edge of town for anyone wanting the quiet version of Lenox. In the center, The Bookstore & Get Lit Wine Bar has sold books for more than three decades under the motto "serving the community since last Tuesday," and pours wine by the glass among the shelves.

Deerfield

Old Main Street in Deerfield has kept its 18th-century face largely intact, a mile of Colonial houses left standing where other towns rebuilt. The Memorial Hall Museum occupies the 1798 original home of Deerfield Academy and, since 1880, has filled 19 rooms with New England antiquities, including the "Bangwell Putt" rag doll, thought to be the oldest in the country, and, in a category of its own, the world's largest pumpkin pie pan.

Just south, the Magic Wings Butterfly Conservatory keeps an 8,000-square-foot glass hothouse at a steady 80 degrees, home to more than 4,000 free-flying butterflies over a koi pond. The Yankee Candle flagship sits nearby with its year-round Bavarian Christmas Village, where indoor snow falls every few minutes, and on Main Street, Richardson's Candy Kitchen has hand-dipped chocolates and made fudge since 1954.

Fairy-Tale Towns Close to Home

What ties these places together is a commitment to the bit. It comes in the form of a carousel that outlasted Coney Island, a farmhouse older than the country that grew up around it, a grain store turned gallery, an academy turned museum. Whether the draw is the whaling captains' Edgartown, the literary streets of Concord, or the Berkshire estates of Stockbridge and Lenox, each town prioritizes authenticity and delights the senses. Leave the Magic Kingdom for the tourists; the real thing is a short drive away.