15 Best Things to Do in Winchendon (MA)

In the 19th century, this town in North-central Massachusetts was known for manufacturing wooden products.

The most successful enterprise to spring up at that time was the Converse Toy & Woodenware Company, making everything from hobby horses to doll furniture, and giving Winchendon the nickname Toy Town, which has stuck to this day.

A rocking horse appears on the town’s official seal, and you can see this emblematic horse, Clyde II, in the center of town under a pavilion.

If you’re yearning for the great outdoors, Winchendon will oblige, with thousands of acres of state forest and wildlife management areas, woven with some 50 miles of trails.

1. Lake Dennison State Recreation Area

A natural body of water, Lake Dennison is part of a giant flood management project by the US Army Corps of Engineers, initiated with the construction of the Birch Hill a couple of miles up the Millers River in 1940.

Most of the surrounding landscape is leased to the Department of Conservation and Recreation (DCR), which is the origin of Lake Dennison as a hub for recreation.

The lake has a swimming beach, open from late May to early September, as well as a boat ramp (non-motorized), a pavilion, and picnic areas on the tranquil shoreline.

There’s a campground close by with 150 sites, while the recreation area is embedded in a vast area of public land, with access to more than 50 miles of trails for hiking, horseback riding, mountain biking, and cross-country skiing.

2. Winchendon History & Cultural Center

The Winchendon Historical Society was founded in 1930 and began a new era in 2000 when the palatial Murdock-Whitney House (c. 1850) was gifted to it.

That original house had been shifted in from Front Street at the turn of the 20th century, and was enlarged at that time into a 22-room mansion.

The interiors abound with carved oak and cherry, along with mirrored mantles and leaded stained glass.

As well as being the main depository for the society’s collections, the house also fascinates fans of the paranormal and welcomes ghost hunts several times a year.

Also part of the Winchendon History & Cultural Center is the Isaac Morse House (135 Front St), where you can browse the range of toys manufactured in Winchendon by the Converse Toy & Woodenware Company between 1887 and 1934.

3. Downtown Winchendon

If you haven’t visited Winchendon’s central commercial area for a while you might be shocked by just how much things have changed for the better.

In the early 2020s the town received state grants to make the arterial Central Street ADA compliant, and there are now new sidewalks, curbing, crosswalks, streetlights, and a bus shelter.

Backed by the steep wooded sides of the Millers River valley, there’s a small but spirited community of local-owned stores and service businesses.

You can shop here for furniture, homewares, antiques, fabrics, flowers and handmade gifts. In October this is the setting for the Winchendon Fall Festival, which we’ll cover in more detail below.

Close by on Whitney Pond, the Winchendon Community Park is a new space for outdoor events. In a pavilion at 226 Front St, you can check out Clyde II, a 1988 replica of a giant rocking horse carved by Morton Converse in 1912.

4. Otter River State Forest

Lake Dennison is just one element in a massive swath of protected public nature, encompassing the southwest of Winchendon, parts of Royalston and Templeton, and bordering the Birch Hill State Wildlife Management Area, which we’ll talk about below.

Otter River State Forest was the first property to be acquired by the State Forest Commission in 1915, and the day-use area was developed by the Civilian Conservation Corps (CCC) during the Great Depression.

You can access more than 50 miles of trails here, discovering huge stands of pine, northern hardwood forest and oak-hickory forest.

There’s wonderful paddling too, along the Millers River, while the day-use facilities are centered on Beaman Pond, where there’s a beach, picnicking areas, pavilion and ballfield.

5. North Central Pathway (Winchendon Rail Trail)

At the end of Summer Drive in downtown Winchendon you can get onto a paved trail that will one day link this town with downtown Gardner 16 miles to the south.

North North Central Pathway is along a former railroad right-of-way, and in Winchendon there’s some beautiful scenery to appreciate.

The trail passes by the south shore of Whitney Pond, and continues southeast through the Millers River valley, twice crossing the river and ending at a picturesque spot by N Ashburnham Rd.

You can pick up the next section from the parking area on Old Gardner Rd, and this stretch leads south through remote woods, parallel to Route 140 as the northern edge of Crystal Lake near downtown Gardner.

6. Winchendon Fall Festival

On a Saturday in October, this lively festival brings thousands of people downtown, closing down a long stretch of Central Street.

The Winchendon Fall Festival was first launched in the 2010s, but has already become a big success, with upwards of 200 vendors setting up along Central Street each year.

This is a showcase for local organizations, clubs, service, as well as small businesses, so there’s a choice of great food and handmade crafts.

You can enjoy some live music, fun contests, and a demonstration by the Winchendon Fire Department, while there’s a host of activities for wee ones, including a tram ride.

7. Monadnock Recreational Rail Trail

Extending the Fitchburg Railroad into New Hampshire, the Monadnock Railroad was initially completed in 1870 connecting Winchendon with Jaffrey, NH. Later part of the Boston and Maine Railroad, the line was finally abandoned in 1972.

Today you can walk or ride for almost ten miles along the railbed through a secluded wooded corridor, from the edge of downtown Winchendon to Jaffrey.

Contrary to some maps, the trail can be accessed from a spur at the end of Poland Avenue. For most of its route the Monadnock Recreational Rail Trail is unpaved or laid with crushed stone, so conditions can be tricky after heavy rain.

8. Birch Hill State Wildlife Management Area

Spread across several parcels, there’s more than 4,500 acres of conserved land open to the public at this WMA on the west side of Winchendon, as well parts of Templeton and Royalston.

The Birch Hill State Wildlife Management Area is composed of wetlands, hardwood and softwood forests, shrublands, as well as historic orchards long reclaimed by nature. You’ll travel across these landscapes on a system of unmarked trails and maintenance roads.

The largest section in Winchendon is on the Millers River, and is a paradise for birding, home to American woodcocks, great blue herons, eastern whip-poor-wills, ruffed grouse, prairie warblers and many more.

9. Toy Town Stained Glass

Just off Route 202 in the northeast of Winchendon there’s a studio specializing in stained glass and fused glass.

If you’re based in the area you can sign up for stained glass or fused glass classes. The main course for beginners lasts several weeks, during which you’ll work on your own project, which comes to life as you develop skills like cutting, grinding, foiling, soldering, framing and polishing.

If you’re just passing by there’s a wonderful gift shop selling a wealth of finished stained glass with all kinds of forms and functions.

10. Beals Memorial Library

Rooted in the Winchendon Scientific and Literary Association in the mid-19th century, Winchendon has had a public library since 1867.

The library bounced around a few locations in the town before moving into a handsome permanent home at 50 Pleasant St in 1913.

Partly funded by Andrew Carnegie and local businessman George L. Beals, this Beaux-Arts building was constructed from Indiana limestone with granite trim.

There’s an auditorium inside with a Chickering grand piano that was donated by Beals in 1914.

A long-term project to make the library fully accessible was completed in 2018, and this amenity continues to shine as a free and open environment, fostering literacy, growth and curiosity. For visitors to the town, one useful service is the free Wi-Fi.

11. Winchendon Community Park

Over the last few years, this park on the east side of downtown Winchendon has gradually taken shape as a top-notch community asset.

On the north shore of Whitney Pond, Winchendon Community Park covers land that belonged to the Winchendon School until late 2016.

You can stroll along a small web of trails, admire the views and enjoy a picnic in a tranquil spot so close to downtown.

The park is intended as a public gathering space, with outdoor performances hosted by the WCP Performing Arts Amphitheater, which was under construction when we compiled this list.

12. Winchendon Farmers’ Market

Winchendon has a contingent of small-scale farmers, makers, gardeners, and more, selling their wares downtown in the summer.

The farmers’ market takes place on Saturday mornings and Thursday afternoons, May through October.

For a sense of what you might find there’s organic seasonal fresh produce, from garlic to corn to zucchini, along with fresh herbs, homemade pickles, jams, teas, and baked goods.

In terms of crafts you can browse knitted items, handmade soaps and lotions, jewelry, home decorations, and a lot more.

13. Lickity Splitz

This seasonal, family-run ice cream stand has been a staple of the summer in Winchendon since 1998.

All of Lickity Splitz’s ice cream is made on site, and this place is regularly listed among the top ice cream shops in the state.

For a small cross-section of the flavors you’ve got frozen pudding, banana chip, black raspberry, rum raisin, blueberry cheesecake, almond joy, butter pecan and peanut butter cup.

There’s a choice of soft serve, sugar-free options, sundaes, parfaits, and flurries, as well as a lineup of savory food. On that side of the menu, a few specialties include the footlong hot dog, the onion rings, and the haddock sandwich.

14. Gardner Municipal Golf Course

The closest public golf course to Winchendon is little more than ten minutes from Lake Dennison in Gardner.

This 18-hole facility dates back to 1936, and has a relatively open layout, with boundless views of the hilly scenery and the stunning Crystal Lake to the south.

There are four sets of tees, so the course can accommodate players of all abilities, and despite the open layout, careful shot placement is always rewarded.

If you need to get into the swing of things there’s a driving range here, along with a putting green, while the clubhouse has a restaurant with a second-story deck overlooking the last few holes.

15. Winchendon Music Festival

In 2016 the composer and multi-instrumentalist, Andrew Arceci launched a concert series in Winchendon, in memory of his father Robert J. Arceci (1950-2015), who had a love for the arts.

The festival consists of live performances in a variety of genres including classical, jazz, folk, world music and period performance.

These involve soloists, small ensembles and chamber orchestras, and take place at evocative venues like the First Congregational Church on Winchendon’s Old Centre Common, and the salon at the Winchen History & Cultural Center.

All Winchendon Music Festival concerts are free to the public.