In the 19th century, this northern Massachusetts town was known for manufacturing wood products.

The most successful company to emerge at this time was the Converse Toy & Woodware Company, which produced everything from hobby horses to doll furniture, giving Winchendon the nickname Toy City, which has still stuck.

The city’s seal features a wooden horse, and you can see this iconic horse, Clyde II, under the observatory in the city center.

If you want to enjoy the great outdoors, Winchendon is the place for you. There are thousands of acres of state forest and wildlife sanctuaries intersected by nearly 80 miles of hiking trails.  

1. Winchendon Fall Festival

On Saturdays in October, this lively festival draws thousands downtown and closes down Long Central Street.

The Winchendon Fall Festival first took place in the 2010s, but it’s already been a huge success, with over 200 vendors lining Central Street each year.

It’s a showcase for local organizations, clubs, services, and small businesses, with great food and handmade crafts.

Enjoy live music, fun competitions, Winchendon Fire Brigade demonstrations, and plenty of activities for the little ones, including tram rides. 

2. Monadnock Recreational Rail Trail

An extension of the Fitchburg Railroad to New Hampshire, the Monadnock Railway was first completed in 1870, linking Winchendon to Jaffrey, New Hampshire. A later part of the Boston and Maine Railroad, the line was finally discontinued in 1972.

Today, you can walk or horseback about 10 miles along the trackbed from the edge of downtown Winchendon to Jaffrey via a secluded, tree-covered walkway.

Unlike some maps, this trail is accessed from a fork at the end of Poland Avenue. The Monadnock Recreational Rail Trail is mostly dirt or gravel, so conditions can get worse after heavy rain.  

3. Birch Hill State Wildlife Management Area

West of Winchendon, part of Templeton and Royalston, this multi-district WMA has more than 11,000 acres of protected land open to the public.

The Birch Hill State Wildlife Management Area consists of wetlands, broadleaf and conifer forests, scrubland, and historic orchards reclaimed by nature. Travel through these landscapes using unmarked trails and maintenance roads.

Winchendon’s largest precinct lies along the Millers River and is a birdwatcher’s paradise. Great woodcocks, gray herons, eastern gray herons, great sparrows, and warblers live here. 

4. Toy Town Stained Glass

Just off Highway 202 in northeast Winchendon, the studio specializes in stained and cast glass.

Local residents can enroll in stained glass and fusing glass classes. The main course for beginners lasts several weeks. During this time, work on your own projects by developing skills such as cutting, sanding, foiling, soldering, framing, and polishing.

Just pass by and you’ll find a great gift shop with an abundance of ready-made stained glass in all shapes and functions.  

5. Beals Memorial Library

Winchendon has its origins in the mid-19th century Winchendon Society for Science and Literature and has had a public library since 1867.

The library moved to several locations around the city, and in 1913 moved into a lovely permanent residence at 50 Pleasant Street.

Funded in part by Andrew Carnegie and local businessman George L. Beals, this Beaux-Arts building was constructed of Indiana limestone with granite decoration.

Inside, there is an auditorium with the Chickering Grand piano donated by Beals in 1914. A long-term project to make the library fully accessible was completed in 2018, and the facility continues to shine as a free and open environment that fosters literacy, growth, and curiosity. Free Wi-Fi is a convenient service for visitors to the city. 

6. Winchendon Community Park

Over the past few years, this park on the east side of downtown Winchendon has gradually evolved into a premier community asset.

Winchendon Community Park, on the north shore of Whitney Pond, occupies land previously owned by the Winchendon School until the end of 2016.

You can walk the small paths, take in the scenery, and enjoy a picnic in a quiet spot near downtown.

The park is intended as a public gathering place and hosts outdoor performances hosted by the WCP Performing Arts Amphitheater, under construction at the time of this listing. 

7. Winchendon Farmers’ Market

Winchendon attracts small farmers, craftsmen, gardeners, and others who sell their wares downtown in the summer.

Farmers markets are held on Saturday mornings and Thursday afternoons May through October.

From garlic, and corn to zucchini, seasonal fresh organic produce, fresh herbs, homemade pickles, jams, teas, baked goods, and more.

Browse the crafts section for knitwear, handmade soaps and lotions, jewelry, home décor, and more.  

8. Lickity Splitz

This seasonal, family-run ice cream parlor has been a Winchendon summer staple since 1998.

All of Lickity Splitz’s ice cream is made locally, and this location is regularly listed among the state’s top ice cream shops.

Frozen Pudding, Banana Chips, Black Raspberry, Rum Rosin, Blueberry Cheesecake, Almond Joy, Butter Pecan, and Peanut Butter Cup are just some of the flavors.

Soft serve ice cream, sugar-free options, sundaes, parfaits, sundaes, and a variety of savory items. This side of the menu features some specialties like footlong hot dogs, onion rings, and haddock sandwiches. 

9. Gardner Municipal Golf Course

The closest public golf course to Winchendon is just 10 minutes from Lake Denison in Gardner.

Dating back to 1936, this 18-hole course features a relatively open plan with unobstructed views of rolling hills and beautiful Crystal Lake to the south.

With four tee groups, the course is suitable for players of all skill levels and despite the open layout, careful shot placement is always rewarded.

If you want to play in earnest, there’s a driving range and putting green here, and the clubhouse has his second-floor terraced restaurant overlooking the last few holes.  

10. Winchendon Music Festival

In 2016, composer and multi-instrumentalist Andrew Arcesi launched a concert series in Winchendon in memory of his art-loving father, Robert J. Arcesi (1950-2015).

The festival will consist of live performances in various genres such as classical, jazz, folk, world music, and historical performances.

Featuring soloists, small ensembles, and chamber orchestras, it takes place in impressive venues such as the First Congregational Church in Winchendon’s Old Center Common and the Salon of the Winchen Historical and Cultural Centre.

All Winchendon Festival concerts are free and open to the public.  

11. Lake Dennison State Recreation Area

Lake Denison is a natural body of water, part of a larger U.S. Army Corps of Engineers flood control project that began in 1940 with the construction of Birch Hill a few miles above the Millers River.

Much of the surrounding land is leased to the Department of Conservation and Recreation (DCR), indicating Lake Denison’s origins as a recreational hub.

The lake has a swimming beach open from late May to early September, as well as boat ramps (not motorized), gazebos, and quiet lakeside picnic areas.

A 150-pitch campground is nearby, and recreation areas are located on extensive public land with access to more than 80 miles of trails for hiking, horseback riding, mountain biking, and cross-country skiing.  

12. Winchendon History & Cultural Center

The Winchendon Historical Society was founded in 1930 and ushered in a new era in 2000 with the donation of the palatial Murdoch Whitney House (circa 1850).

The original home was relocated from Front Street by the early 20th century, at which point he expanded into a 22-room mansion.

Interiors are carved in oak and cherry wood and feature mirrored mantelpieces and stained-glass windows.

In addition to being the primary repository for the Society’s collection, the house attracts fans of the paranormal and hosts ghost hunts several times a year. The Winchendon Historical and Cultural Center also includes the Isaac Morse House (135 Front Street), where you can browse a variety of toys manufactured in Winchendon between 1887 and 1934 by the Converse Toy & Woodware Company can. 

13. Downtown Winchendon

Those who haven’t visited Winchendon’s CBD in a while may be shocked at how much things have changed for the better.

In the early 2020s, the city received a federal grant to make the Central Avenue highway compliant with its ADA and now has new sidewalks, curbs, crosswalks, streetlights, and bus stops.

Nestled on the steep, forested slopes of the Millers River Valley is a small but vibrant community of local shops and hospitality.

Here you can buy furniture, homewares, antiques, fabrics, flowers, and handmade gifts. The Winchendon Fall Festival is held here in October. More on this below. Winchendon Community Park near Whitney Pond is a new outdoor venue. At the pavilion at 226 Front Street, you can see Clyde II, a replica of his 1988 giant rocking horse sculpted by Morton Converse in 1912.  

14. Otter River State Forest

Lake Denison is only part of a largely protected public wilderness area southwest of Winchendon, including parts of Royalston and Templeton, and borders the Birch Hill State Wildlife Management Area, described below.

The Otter River State Forest was the first land acquired by the State Forest Commission in 1915, and the daytime area was developed by the Civilian Conservation Corps (CCC) during the Great Depression.

Here you can access over 80 miles of hiking trails that discover vast pine forests, northern hardwood forests, and oak-hickory forests.

Paddling along the Millers River is also great. Day-use facilities are also centered around Biman Pond, which includes a beach, picnic areas, pavilions, and ball fields. 

15. North Central Pathway (Winchendon Rail Trail)

At the end of Summer Drive in downtown Winchendon, you’ll hit a paved trail that will one day connect the town to downtown Gardner, 26 miles south.

The North-North Central Pathway runs along former railroad tracks and Winchendon has some beautiful scenery to admire.

The trail bypasses the south bank of Whitney Pond and continues southeast through the Millers River Valley, a river he crosses twice, ending at the scenic spot of N Ashburnham Road.

The following sections can be picked up from the Old Gardner Rd parking lot. This section heads south through remote forest and parallels US 140 at the northern end of Crystal Lake near downtown Gardner.