15 things to do in Cheshire (CT)

The historic center of this pleasant town between New Haven and Hartford is located in stately parkland next to the First Congregational Church (1827) and the Greek Revival City Hall.

In June, the green space hosts a small strawberry festival, suitable for the many fruit growing farms in the area, with one Drazen Orchards farm open for picking season in August, September and October.

In and around Cheshire, there is plenty of natural drama at the towering Roaring Creek Falls and the basalt overlook at Metacomet Ridge.

But what attracts people from the US and beyond is the amazing collection at the Barker Museum of Characters, Comics and Cartoons, which we discuss below.

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

1. Buck Museum of Characters, Comics and Cartoons

Buck Museum of Characters, Comics and Cartoons

The Barker Museum of Characters, Comics and Cartoons is just the kind of attraction you’d expect to find in a small town, an incredible hodgepodge of all your favorite pop culture figures.

Founded by local businessman Herbert Barker (1929-2019), the collection includes 80,000 pieces over 14 years, including toys, dolls, lunch boxes, wooden decoupage, PEZ dispensers, board games, puppets, cards , Cell Art and Comics.

You’re sure to find something that will linger in your memory and the kids will be in awe.

It’s also fun to draw the evolution of beloved characters like Mickey Mouse, Batman, and Popeye from their origins.

The museum is open Wednesday through Saturday.

2. Roaring Creek Park

Roaring Creek Park

Just a few miles from quaint town green, is one of the tallest waterfalls in Connecticut.

Here, roaring streams wash down 24-meter-high cliffs of freshly deciduous woodland.

See if you can schedule your visit after a day or two of steady rain, when traffic and noise are most impressive.

When the area was settled by Europeans in the 17th century, the cliffs were cleared of trees, and in the 18th century the turbulent water of the roaring stream was used by mills.

Today, there is little sign of human habitation, save for the eerie fireplace and chimney of a long-forgotten house, and the tray-like bridge on the Cheshire Town trail.

The routes from town are mostly uphill and can be a bit much for smaller walkers.

3. Farmington Canal Heritage Walk

Farmington Canal Heritage Walk

In the 1820s, a group of merchants joined forces to build a private canal from New Haven to Farmington, now in Hartford County.

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

This was incorporated into the New York, New Haven, and Hartford Railroad in 1887, and by the second half of the 20th century, most of the railroad was out of service.

The Farmington Canal Heritage Trail is 81.2 miles of the track bed, with some gaps everywhere.

Cheshire is special because it retains Lock 12, one of the only remaining pieces of Connecticut’s canal infrastructure.

At Lock 12 Historical Park, you can see restored locks, the lock butler’s house, and a museum full of canal-related memorabilia.

4. Quinnipiac Trail

Quinnipiac Trail

Starting in Prospect and ending in North Haven, the 24-mile Quinnipiac Trail runs through Cheshire and leads you to some amazing natural monuments in and around town.

A Connecticut Blue Flame Trail, the route is marked by light blue vertical flames, usually in trees, as part of a system established in 1929. While most of the walk is in gentle woodland, things get more challenging around Cheshire. The ridges take you over some remote basalt formations at Metacomet Ridge and close to the spectacular gorge of Roaring Creek Falls.

5. Cheshire Historic District

Cheshire First Congregational Church

The town is in the most beautiful location south of the junction of Main Street and Academy Road.

Here, at the foot of the First Congregational Church of Cheshire (1827) are typical New England greens. Designed by Waterbury architect David Hodley (1774-1839), this gleaming white clapboard building has a bold Ionic portico and four fluted columns.

Opposite the green is the Greek Revival Town Hall, which dates back to 1867, unusually late for this architectural style.

Most of the buildings in the surrounding Cheshire Historic District cover 35 acres and were built in the mid 19th century, but there is a beautiful late 18th century commercial building on South Street.

6. Cheshire Historical Society

Cheshire Historical Society

Next door to First Congregational Church in bucolic green is Hitchcock-Phillips House, a fine Georgian building built in 1785 that is home to the Cheshire Historical Society.

Built by businessman and famous citizen Rufus Hitchcock, it has five bays, three skylights (added in 1925) and one built in 1820 by Hitchcock’s son William Rufus Hitchcock Left and right built flanks. On Sundays or pre-arranged visits, you can look around and admire period accessories (beehive ovens), paintings, prints, 19th century clocks from the Cheshire Watch Company, household items, toys, guns, quilts and other textiles.

The most valuable work in the house is the painting on the mantelpiece in the dining room, depicting the heart of Cheshire, commissioned by Rufus Hitchcock in 1810. Also of note are the 1775 grandfather clock and the travel desk used by 13th President Millard Fillmore.

7. Bartleham Recreation Area

Bartleham Recreation Area

If you’re looking to get some exercise outdoors, your first choice in Cheshire is this well-appointed park, just across from Cheshire High School on Route 10. In a nutshell, the Bartham Recreation Area has a 90-foot baseball field, soccer and lacrosse fields, community pool, skate park, and playground for kids in motion.

In winter, the Greg Sherner Memorial Rink is open 7 days a week and is free to the public, but you’ll need to bring your own gear.

Stop for a while and there’s the Bartham Pavilion and grassy picnic area.

On four consecutive Fridays in July and August, you can take part in outdoor concerts, usually tribute shows, on the field.

The farmers market is also open every Thursday from 16:30 to 18:00, just across the road at the Cheshire Parks and Recreation Building.

8. Hubbard Park

Hubbard Park, Meriden

This stunning park, a blend of scenic and mountain wilderness, was the brainchild of Meriden industrialist Walter Hubbard.

He donated the 1,800-acre hanging hill at the turn of the 20th century and went to great lengths to turn it into a haven for the people of his hometown.

Hanging Mountain is a prominent basalt formation connected to the narrow linear Metacomet ridge that dates back 200 million years and interrupts the landscape from Long Island Sound to the Massachusetts-Vermont border.

Hubbard Park has trails suitable for winter hiking, biking, and cross-country skiing, as well as more formal spaces such as husks in flower beds.

On the last weekend of April, it’s the backdrop for the Meriden Daffodil Festival, with rides, judging arts and crafts, food trucks, fireworks and more than 600,000 daffodils in bloom.

9. Delason Orchards

Delason Orchard

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

Over time, current farm owner Gordon Drazen replanted the farm’s orchards on trellis support systems to maximize sun exposure and employed integrated pest management to minimize pesticide use.

Drazen Orchards has had a summer picking season since the early 1950s.

It usually runs from August to mid-October and serves blueberries, Asian and Italian plums, yellow and white nectarines, peaches, papayas and pears.

Drazen Orchards planted about 14 apple varieties, including Macoun, Golden Delicious, Honeycrisp, Gala, Cortland and Zestar, which were ready between August 12 and October 18. From August to November, stop by the farm stand for freshly picked fruit, vegetables and herbs and flowers, as well as cider doughnuts, apple pie, honey and cider.

10. Sleeping Giant State Park

Towers of Sleeping Giant State Park

Part of the Quinnipiac Trail and Metacomet Ridge is a strange basalt formation in South Cheshire.

The sleeping giant looked exactly like it sounded: a massive figure lying on its back, head, chin, chest, hips, knees and feet jutting out of the landscape.

There are more than 30 miles of trails through the state park, including the 5-mile Quinnipiac Trail.

Some plants not commonly found in Connecticut thrive in calcium-rich soil further below, while chestnut oaks grow among ferns and grasses on the dry, sun-drenched upper ridges.

The giant’s head has a 120-meter cliff, and the highest point is the left hip at 225 meters, where you can climb an observation tower built during the Great Depression and survey the Quinnipiac and Mill River valleys.

11. Sanford Hills

The Naugatuck State Forest is huge, spreading over 4,153 acres across eight different towns including Cheshire.

The forest consists of five blocks, the easternmost of which is the Sanford Hills block.

The peak here is 270 meters high and also belongs to Metacomet Ridge, the highest point of the Quinnipiac Trail that crosses its ridge.

If you’re coming by car, access to the Quinnipiac Trail couldn’t be easier, as it’s right next to the parking lot on Bethany Hill Road, southwest of town.

You’ll wander among tall broadleaf trees such as hickory, beech, oak, birch, and maple, home to dozens of bird species, from barred owls to great crested flycatchers and turkey buzzards.

12. Cheshire Park

This quiet local park is slightly off Route 10 and close to the Southington Town Line.

A quarter of Cheshire Park’s 75 acres is devoted to active recreation.

So you have softball fields, basketball courts, and tennis courts.

There are separate playgrounds for children ages 1 to 4 and 5 to 12, as well as a gazebo and picnic area.

There is also an amphitheater on hand that hosts small community events during the summer.

13. Cheshire Valley Farm

Cheshire Hollow Farm

Located in the idyllic north end of Cheshire, this working farm sells pumpkins and Christmas trees in late October and November.

Bring your kids along as there are friendly farm animals like miniature horses, pygmy goats, miniature cows, pot-bellied pigs, rabbits and chickens.

The farm is closed to the public at other times, but can be visited through a pre-arranged “Family Farm Tour” lasting 90 minutes, during which you can raise, pet and feed the farm’s resident animals.

14. Whippersnapper’s Play Gym

Whippersnapper's Playhouse

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

Here children can explore, learn and develop motor skills through play, music, creative movement and crafts.

There are also schedules for yoga, gymnastics and cheerleading, as well as slots for toddlers and children with special needs.

There is a day camp in the summer that welcomes guests from police and fire departments or aquariums and farms with live animals almost every day.

Outside the summer months, you can also take Open Play classes on weekends only for $7 per child.

15. Cheshire Strawberry Festival and Craft Fair

Cheshire Strawberry Festival

On the second Saturday in June, a strawberry-themed celebration takes place on the green field in front of the First Congregational Church.

Now in its ninth decade, this highly supported event features over 30 curated arts and crafts booths, live music and many activities to keep kids entertained, from face painting to bouncy castles.

As a strawberry festival, there are plenty of tempting food and drinks here, such as farm fresh strawberries with whipped cream, chocolate strawberries, strawberry shortcake, strawberry smoothies, and delicious treats like burgers and hot dogs.

Where to Stay: Best Hotels in Cheshire, CT (CT)
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