15 Best Things to Do in Cheshire (CT)

The historic center of this agreeable small town between New Haven and Hartford is on a dignified green. Reaching back centuries, this space is bordered by the First Congregational Church (1827) and a Greek Revival Town Hall.

In June the green holds a little strawberry festival, which is appropriate for the many fruit-growing farms in the area. One of these, Drazen Orchards, is open for a pick-your-own season in August, September and October.

There’s a lot of natural drama both in and near Cheshire, at the high Roaring Brook Falls and the basalt overlooks of the Metacomet Ridge.

Something that draws people from across the United States and beyond is the amazing stash of collectibles at the Barker Character, Comic and Cartoon Museum, which I’lll talk about first.

Let’s explore the best things to do in Cheshire:

1. Barker Character, Comic and Cartoon Museum

Just the sort of attraction I hope to find in a small town, the Barker Character, Comic and Cartoon Museum is a mind-boggling jumble of memorabilia for all your favorite pop culture characters.

The collection was begun by local businessman Herbert Barker (1929-2019) and comprises 80,000 pieces across some 15 decades. These include toys, dolls, lunch boxes, wooden cut-outs, PEZ dispensers, board games, marionettes, cards, cell art and comics.

You’re sure to find something that takes you down memory lane, while children will be in awe.

It’s also fascinating to chart the evolution of beloved characters like Mickey Mouse, Batman and Popeye from their very origins. The museum is open Wednesday to Saturday.

2. Roaring Brook Park

Only a couple of miles from the quaint town green is one of the tallest waterfalls in Connecticut. Here Roaring Brook crashes 78 feet down a cliff in fresh deciduous woodland.

I’d try to time a visit after a day or two of steady rainfall when the flow and noise are most impressive.

When the area was settled by Europeans in the 17th century the cliff was cleared of trees. Later, in the 18th century the Roaring Brook’s fast-flowing waters were harnessed by a mill.

Today there’s little sign of human habitation apart from the eerie hearth and chimney of a long forgotten house, and pallet-style bridges on the Cheshire Town Trail. The route from the town center is mostly uphill and might be a bit much for the youngest walkers.

3. Farmington Canal Heritage Trail

In the 1820s a group of businessmen teamed up to construct a private canal from New Haven to Farmington, now in Hartford County.

Within little more than a decade, railroads had become a faster and more economical mode of transport. So by the late 1840s the New Haven and Northampton Company had laid down a line on the canal bed.

This was consolidated into the New York, New Haven and Hartford Railroad in 1887, and by the second half of the 20th century had mostly fallen out of use.

The Farmington Canal Heritage Trail is on 81.2 miles of the railbed, with a few gaps here and there.

I have to point out that Cheshire is special. On the path in the town is Lock 12, one of the last remaining pieces of the canal infrastructure in Connecticut.

At the Lock 12 Historic Park you can see the restored lock, as well as the preserved lock-keeper’s house.

4. Quinnipiac Trail

Starting in Prospect and ending in North Haven, the 24-mile Quinnipiac Trail passes through Cheshire. On this path you’ll reach some awe-inspiring natural monuments in and around the town.

A Connecticut Blue-Blazed trail, the route is marked by light blue vertical blazes, generally on trees, as part of a system established back in 1929.

Although much of the walk is in gentle woodland, things get a bit more challenging around Cheshire. It’s one of the reasons I love hiking in this town.

Here the trail carries you over some of the outlying basalt landforms on the Metacomet Ridge, and close to the spectacular chasms at Roaring Brook Falls.

5. Cheshire Historic District

To my mind, the town is at its prettiest just south of the junction of Main Street and Academy Road.

At this spot there’s a typical New England green laid out at the foot of the First Congregational Church of Cheshire (1827). This gleaming white building was designed by the Waterbury architect David Hoadley (1774-1839), and has a bold Ionic portico with four fluted columns.

Facing off across the green is the Greek Revival Town Hall, dating to 1867, unusually late for this building style.

Much of the architecture in the surrounding Cheshire Historic District, spread across 35 acres, is from the mid-19th century. Still, there’s a beautiful commercial building from the end of the 18th century down South Main Street.

6. Cheshire Historical Society

Next door to the First Congregational Church on the pastoral green is the Hitchcock-Phillips House. This refined Georgian residence dates to 1785, and houses the Cheshire Historical Society.

It was built by the merchant and prominent citizen Rufus Hitchcock and has five bays, three dormer windows (added 1925) and a wing that was constructed by Hitchcock’s son William Rufus Hitchcock around 1820.

You can pay a visit on Sundays or by prior arrangement to look around and appreciate the period fittings.

On display are paintings, engravings, household items, toys, firearms, quilts ,and other textiles. Above all, I was intrigued by the 19th-century timepieces made by the Cheshire Watch Co.

The most valuable piece in the house is the over-mantel painting in the dining room, depicting the center of Cheshire. This was commissioned by Rufus Hitchcock in 1810. Also noteworthy are a grandfather clock from 1775 and a traveling desk used by the 13th President Millard Fillmore.

7. Bartlem Recreation Area

If you’re up for some exercise in the open air, the go-to in Cheshire is this well-equipped park just across from Cheshire High School on Route 10.

Just for a brief summary, the Bartlem Recreation Area has a 90-foot baseball diamond, fields for soccer and lacrosse, a community pool, skate park, and a Kids in Motion playscape. I haven’t seen many public parks so well looked after.

Come winter the Greg Schena Memorial Ice Skating Rink is open seven days a week. This facility is free to the public, though you’ll need to bring your own gear. For a pause there’s the Bartlem Pavilion and a grassy picnic area.

Over four consecutive Fridays in July and August you can come for outdoor concerts on the field, normally by tribute acts.

8. Hubbard Park

This astonishing park, blending landscaped areas and mountainous wilderness, was the brainchild of Meriden industrialist Walter Hubbard.

He donated this 1,800-acre patch of the Hanging Hills at the turn of the 20th century. The man went to great lengths and expense to turn it into a haven for the people of his home town.

The Hanging Hills are a prominent basalt formation attached to the narrow, linear Metacomet Ridge. This dates back 200 million years and interrupts the landscape from Long Island Sound to the Massachusetts-Vermont border.

There are trails in Hubbard Park for hiking, cycling and cross-country skiing in winter. Among the woods are more developed spaces like the bandshell ensconced in flower beds.

On the last weekend in April this is the backdrop for the Meriden Daffodil Festival. It’s my recommended time to come, with amusement rides, juried arts and crafts, food trucks, fireworks, and more than 600,000 blooming daffodils.

9. Drazen Orchards

In the Drazen family since 1951, Drazen Orchards is on land that was first planted in the early 19th century.

Over time the current farmer-in-chief Gordon Drazen replanted the farm’s orchards on a trellis support system for maximum exposure to sunshine, and adopted Integrated Pest Management to minimize the use of pesticides.

Drazen Orchards has opened for summer pick-your-own seasons since the early 1950s. Typically this will run from late July to mid-October, for blueberries, Asian and Italian prune plums, yellow and white nectarines, peaches, quinces and pears.

Drazen Orchards grows some 14 apple varieties. Among them are Macoun, Golden Delicious, Honeycrisp (my fave), Gala, Cortland and Zestar, ready from around mid-August to mid-October.

You can stop at the farm stand between July and November for freshly picked fruit, vegetables, herbs and flowers. Don’t miss the chance to pick up their awesome baked goods, including apple cider donuts and apple pies.

10. Sleeping Giant State Park

On the Quinnipiac Trail and also part of the Metacomet Ridge is a curious basalt landform to the south of Cheshire.

The Sleeping Giant looks exactly how it sounds: An enormous figure lying on its back, with head, chin, chest, hips, knee and feet all protruding from the landscape.

There are more than 30 miles of trails coursing through the state park, including five miles of the Quinnipiac Trail.

Some plants unusual for Connecticut thrive in the calcium-rich soils further down. Meanwhile on the dry, sun-baked upper ridges there are chestnut oaks over ferns and grasses.

There’s a 394-foot cliff at the giant’s head, while the highest point is the left hip at 738 feet. There you can scale an observation tower constructed in the Great Depression. From here you can survey the Quinnipiac and Mill River Valleys for miles.

11. Mount Sanford

The Naugatuck State Forest is immense, unfolding over 4,153 acres in eight different towns, including Cheshire.

The forest comprises five blocks, the easternmost portion of which is the Mount Sanford block.

The peak here, rising to 886 feet, also belongs to the Metacomet Ridge. In fact, it’s the highest point on the Quinnipiac Trail, which traverses its ridge.

If you’re coming by car it couldn’t be easier to get onto the Quinnipiac Trail as it runs next to the parking lot on the Bethany Mountain Road in the very southwest of the town.

Safe to say, I’ll never tire of hiking here. You walk among tall broadleaf trees like hickory, beech, oak, birch and maple. These woods support scores of bird species, from barred owls to great-crested flycatchers and turkey vultures.

12. Cheshire Park

This local public park is slightly withdrawn from Route 10, close to the Southington Town line.

A quarter of Cheshire Park’s 75 acres are set aside for active recreation. So you’ve got softball fields, a basketball court, tennis courts, and pickleball courts.

There are separate playgrounds for kids aged 1 to 4 and 5 to 12, as well as a pavilion and picnic area. Also on hand is an amphitheater, putting on small community events in the summer.

The less developed corners of Cheshire Park are in a parcel of woodlands, with a small network of trails to explore.

13. Cheshire Hollow Farm

This working farm is in the idyllic north end of Cheshire, selling pumpkins and Christmas trees in the month of October and from the end of November respectively.

I’d bring the children when you come by, as there are friendly barnyard animals to meet. When I visited there were miniature horses, pygmy goats, miniature cattle, pot-bellied pigs, rabbits, and chickens.

Some are rescued and some have come from breeders, but all have been raised as pets. For instance, one of the pigs will happily follow you around the farm on your tour.

The farm is closed to the public at other times, but can be visited on a pre-arranged “Family Farm Tour”. This experience lasts 90 minutes when you can hold, pet and feed the farm’s resident animals.

14. Whippersnapper’s Play Gym

This indoor soft playground organizes all sorts of activities to help children develop self-esteem and confidence through play, all in a safe, non-competitive environment.

Here children can explore, learn and develop motor skills with games, music, creative movement and arts and crafts.

There’s also a schedule of classes for yoga, gymnastics and cheerleading, and slots for toddlers and children with special needs.

Look out for the day camps during school breaks. These receive special guests almost daily from the police and fire department, or from aquariums and farms, bringing live animals.

Outside the summer months you can also just show up on weekends for Open Play sessions, at $14 per child when I went to press.

15. Cheshire Strawberry Festival and Craft Fair

Taking over the green in front of the First Congregational Church there’s a strawberry-oriented celebration on the second Saturday of June. When I wrote this article, this traditional New England celebration was deep into its ninth decade.

The event involves more than 30 curated arts and craft stalls in a beautiful setting. There’s live music and plenty of things to keep children entertained, from face-painting to bounce houses.

And being a strawberry festival there’s plenty of enticing food and drink, like farm-fresh strawberries with whipped cream, chocolate covered strawberries, strawberry shortcake, and strawberry smoothies. If you’re in need of something savory, you’ve got goodies like burgers and hot dogs.