'Toy Town USA' Is A Nostalgic Massachusetts Escape With Shops, Trails, And Historic New England Charm

With a moniker like "Toy Town, U.S.A.," you might envision walking, life-sized nutcrackers stalking the streets, living rocking horses, and legions of dead-eyed dolls staring from shop windows. While this image of Winchendon, Massachusetts, isn't quite accurate, the town was once filled with old-timey toys of the type you might imagine. From the late 19th century to the early 20th century, Winchendon became such a hub of toy manufacturing that The New York Times in 1914 called it "the cradle of the toymaking industry in America." And while most of the toys have long gone — aside from stores like Robin's Retro Dolls – Winchendon retains enough quirk, history, and surrounding nature to make it worth a visit.

Winchendon's unusual toy-focused history centers largely on Morton E. Converse & Son, a local toy manufacturer. The family-owned business opened in 1878 as a small wooden toy maker and evolved into a full-scale industrial toymaking operation. One of its key products, a wooden hobby horse dubbed Clyde in 1912, still stands west of downtown as a landmark. After Morton died and his son retired in 1931, a series of business mergers brought the toy production to an end. But not before the company helped beautify the town and plant 1,000 trees, a gesture that helped shape Winchendon into what it is today. 

Nowadays, visitors to Winchendon can soak in this history along Central Street, which contains a mixture of Colonial-era buildings and red-brick structures. Aside from Robin's Retro Dolls, nearby businesses reference "Toy Town" in their names, including the very local Toy Town Pub. Meanwhile, the area around Winchendon is also rich in parks, nature preserves, walkable trails, and bodies of water such as Lake Dennison.

Visitors to Winchendon will want to head first to its shops and restaurants along Central Street. There, Sippin Serendity, a coffee shop, operates in an old house with wood floors, sofas and lounges, and an overall homey décor. Not Just Produced, a small grocery, exudes New England charm and sells handcrafted goods from local artisans. The turn onto Front Street reveals an extremely picturesque strip that includes the two-story Winchendon Town Hall next to Monument Park, which contains memorials to veterans. 

The junction of Central and Front is lined with buildings that add grandeur and elegance to the area while highlighting Winchendon's history. The muscular yet graceful neoclassical facade of Beals Memorial Public Library, built in 1913, houses the town's library and overlooks community events on its lawn. Right next door is the Winchendon History and Cultural Center, a sumptuously decorated early 20th-century Colonial home available to book for events like weddings or even ghost hunts. Nearby sits the Isaac Morse House, a 1790-built structure that serves as the Winchendon History and Cultural Center's Toy Museum and Gift Shop. In 2000, prominent local Rohanna gave her family's fantastically beautiful, 1850-built Murdock-Whitney House to Winchendon, adding to this collection of historical buildings.

Far from stopping there, the town of Winchendon published its 201-page Downtown Winchendon Revitalization Strategy in 2014. Recommendations included rebranding from Toy Town to Winchendon Village, expanding sidewalks to include bike lanes, rezoning to encourage investors, creating themed crosswalks across town, and more. Such changes could help lay the foundation for an inviting, prototypical New England getaway village.

Massachusetts isn't lacking in forested vistas and hikable park paths, and that includes Winchendon. Aside from 16 National Park Service units, many of which are clustered around Boston, the rest of the state is teeming with greenery, from the beloved and awesomely-named Purgatory Chasm to the dense and expansive Savoy Mountain State Forest. While Winchendon doesn't have big-name parks, it's surrounded in every direction by woods, trails, and bodies of water.

The easiest in-town trail for visitors is the Ware River Rail Trail, which runs along Millers River on the south side of town and connects to Millers Reservoir and Tannery Pond. The flat, often-overlooked trail weaves beneath the tree canopy and links to the larger, paved, roughly 5.5-mile Winchendon Rail Trail that heads into the countryside. Back near town, Whitney Pond is home to Winchendon Community Park on the north side and the North Central Pathway set of walking trails on the south side.  

For those who want to venture a little farther, Lake Dennison and its 150 campsites and beach are only 6 minutes from Winchendon by car. A lake visit would be an ideal way to balance out a town jaunt, especially for families. Aside from campgrounds and general outdoor revelry, a full suite of activities is available at Lake Dennison: Hiking, mountain biking, canoeing, fishing, hunting, horseback riding, snowmobiling, and cross-country skiing. Chances are kids will have a toy or gadget in tow to remind you of Winchendon's heyday as Toy Town, U.S.A.