Top 15 Attractions and Activities in Cheshire, CT

The historic center of this charming town, situated between New Haven and Hartford, boasts a distinguished green space. This area, which dates back centuries, is bordered by the First Congregational Church (1827) and a Greek Revival Town Hall.

In June, the green space hosts a modest strawberry festival, in alignment with the numerous fruit-growing farms in the vicinity. One such farm, Drazen Orchards, opens its gates for a pick-your-own season from August through October.

Cheshire is surrounded by significant natural beauty, exemplified by the striking Roaring Brook Falls and the basalt overlooks of the Metacomet Ridge.

A notable attraction that garners attention from visitors across the United States and beyond is the remarkable collection at the Barker Character, Comic and Cartoon Museum, which is discussed first.

Let’s delve into the premier attractions in Cheshire:

1. Barker Character, Comic and Cartoon Museum

Source: Barker Character, Comic And Cartoon Museum / facebook

Characteristic of the attractions I appreciate in a small town, the Barker Character, Comic and Cartoon Museum presents an astonishing collection of memorabilia featuring beloved pop culture characters.

The collection, initiated by local entrepreneur Herbert Barker (1929-2019), encompasses 80,000 items spanning approximately 15 decades. This includes toys, dolls, lunchboxes, wooden cut-outs, PEZ dispensers, board games, marionettes, cards, cell art, and comics.

Visitors are likely to encounter items that evoke nostalgia, while younger guests will be captivated by the displays.

It is also intriguing to trace the development of iconic characters such as Mickey Mouse, Batman, and Popeye from their inception to the present day. The museum operates from Wednesday to Saturday.

2. Roaring Brook Park

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Located just a few miles from the picturesque town green, Roaring Brook Park features one of Connecticut’s tallest waterfalls. Here, Roaring Brook cascades 78 feet down a cliff amidst fresh deciduous woodland.

Timing a visit after a day or two of consistent rainfall will enhance the experience, as the flow and sound become most impressive during these times.

During its settlement by Europeans in the 17th century, the cliff was cleared of trees, and in the 18th century, the rapid currents of Roaring Brook were utilized by a mill.

Today, little evidence of human activity remains apart from the haunting hearth and chimney of a long-forgotten home, alongside pallet-style bridges on the Cheshire Town Trail. The journey from the town center is primarily uphill, which may prove challenging for younger hikers.

3. Farmington Canal Heritage Trail

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In the 1820s, a consortium of businessmen endeavored to construct a private canal connecting New Haven to Farmington, situated in Hartford County.

Within a decade, railroads emerged as a quicker and more cost-effective means of transportation. Consequently, by the late 1840s, the New Haven and Northampton Company established a rail line over the former canal bed.

This line was incorporated into the New York, New Haven, and Hartford Railroad in 1887, and by the latter half of the 20th century, it had largely fallen into disuse.

The Farmington Canal Heritage Trail follows 81.2 miles of the railbed, with a few gaps along the way.

Cheshire possesses a unique feature on the path; Lock 12 stands as one of the last remaining elements of Connecticut’s canal infrastructure.

At Lock 12 Historic Park, visitors can observe the restored lock along with the preserved lock-keeper’s residence.

4. Quinnipiac Trail

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Beginning in Prospect and concluding in North Haven, the 24-mile Quinnipiac Trail traverses through Cheshire, leading hikers to awe-inspiring natural monuments within and surrounding the town.

This Connecticut Blue-Blazed trail, marked by light blue vertical blazes typically positioned on trees, is part of a system established back in 1929.

Although the majority of the journey is through gentle woodland, the terrain becomes more demanding around Cheshire, which is one of the reasons that make hiking in this town particularly appealing.

The trail takes you across some of the outlying basalt formations on Metacomet Ridge and in close proximity to the stunning chasms at Roaring Brook Falls.

5. Cheshire Historic District

Source: en.wikipedia.org

In my view, the town showcases its finest aesthetics just south of the intersection of Main Street and Academy Road.

Here lies a quintessential New England green, enhanced by the presence of the First Congregational Church of Cheshire (1827). This immaculate white structure, crafted by Waterbury architect David Hoadley (1774-1839), features a prominent Ionic portico supported by four fluted columns.

Across the green stands the Greek Revival Town Hall, constructed in 1867, which is relatively late for that architectural style.

Much of the architecture within the adjacent Cheshire Historic District, which spans 35 acres, originates from the mid-19th century. Additionally, a beautifully preserved commercial building from the late 18th century is situated along South Main Street.

6. Cheshire Historical Society

Source: Cheshire Historical Society

Adjacent to the First Congregational Church on the pastoral green stands the Hitchcock-Phillips House, a refined Georgian establishment dating back to 1785, which serves as the headquarters for the Cheshire Historical Society.

This residence was constructed by renowned merchant Rufus Hitchcock and features five bays, three dormer windows (added in 1925), and an extension built by Hitchcock’s son, William Rufus Hitchcock, around 1820.

Visitors can explore the house on Sundays or through prior arrangement to appreciate its period furnishings.

The exhibits include paintings, engravings, household items, toys, firearms, quilts, and various textiles. I was particularly fascinated by the 19th-century timepieces crafted by the Cheshire Watch Co.

The most significant artifact in the house is an over-mantel painting in the dining room, showing the center of Cheshire, commissioned by Rufus Hitchcock in 1810. Additionally, there is a grandfather clock from 1775 and a traveling desk utilized by the 13th President, Millard Fillmore.

7. Bartlem Recreation Area

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For those seeking outdoor physical activity, the primary destination in Cheshire is this well-maintained park located directly across from Cheshire High School on Route 10.

In short, the Bartlem Recreation Area features a 90-foot baseball diamond, fields for soccer and lacrosse, a community pool, skate park, and a Kids in Motion playscape. Few public parks receive the same level of care as this one.

During winter, the Greg Schena Memorial Ice Skating Rink is operational seven days a week. This facility is free to the public; however, visitors must provide their own equipment. The park also offers the Bartlem Pavilion and a grassy picnic area for relaxation.

Over four successive Fridays in July and August, outdoor concerts are held in the field, typically featuring tribute acts.

8. Hubbard Park

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This remarkable park, blending manicured landscapes with mountainous wilderness, was envisioned by Meriden industrialist Walter Hubbard.

He generously donated this 1,800-acre region of the Hanging Hills in the early 20th century, going to great lengths to transform it into a sanctuary for the people of his hometown.

The Hanging Hills are a notable basalt formation that is part of the narrow, linear Metacomet Ridge, a geological feature dating back 200 million years that shapes the landscape from Long Island Sound to the Massachusetts-Vermont border.

The park contains trails suitable for hiking, cycling, and cross-country skiing in winter, alongside developed spaces such as the bandshell nestled within floral beds.

During the last weekend of April, this area serves as the backdrop for the Meriden Daffodil Festival, an event I highly recommend attending, featuring amusement rides, juried arts and crafts, food trucks, fireworks, and over 600,000 blooming daffodils.

9. Drazen Orchards

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Owned by the Drazen family since 1951, Drazen Orchards occupies land that was initially cultivated in the early 19th century.

Over the years, the current farmer, Gordon Drazen, has restructured the farm’s orchards on a trellis support system to enhance sunlight exposure and has implemented Integrated Pest Management practices to reduce pesticide use.

Drazen Orchards has welcomed visitors for pick-your-own seasons since the early 1950s, typically running from late July to mid-October for blueberries, Asian and Italian prune plums, yellow and white nectarines, peaches, quinces, and pears.

This orchard grows approximately 14 varieties of apples, including Macoun, Golden Delicious, Honeycrisp (a personal favorite), Gala, Cortland, and Zestar, which are available from mid-August to mid-October.

Visitors can stop at the farm stand between July and November to purchase freshly picked fruits, vegetables, herbs, and flowers. Be sure to try their delightful baked goods, such as apple cider donuts and apple pies.

10. Sleeping Giant State Park

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The Quinnipiac Trail, also part of the Metacomet Ridge, features a distinctive basalt landform situated to the south of Cheshire.

This geological formation, known as the Sleeping Giant, resembles the figure of a massive being lying on its back, with its head, chin, chest, hips, knees, and feet protruding from the landscape.

The state park encompasses over 30 miles of trails, including five miles along the Quinnipiac Trail.

In the calcium-rich soils further down, some plants unique to Connecticut flourish, while the dry, sun-baked upper ridges are home to chestnut oaks flourishing amidst ferns and grasses.

A 394-foot cliff marks the giant’s head, while the highest elevation, at 738 feet, is located at the left hip. At this point, visitors can ascend an observation tower constructed during the Great Depression, offering panoramic views of the Quinnipiac and Mill River Valleys.

11. Mount Sanford

The Naugatuck State Forest spans an impressive 4,153 acres across eight different towns, including Cheshire.

Consisting of five distinct blocks, the easternmost section is designated as the Mount Sanford block.

The peak here rises to 886 feet and is part of the Metacomet Ridge, representing the highest point along the Quinnipiac Trail that traverses the ridge.

Accessing the Quinnipiac Trail by car is easy as it runs adjacent to the parking lot on Bethany Mountain Road, located in the southwest part of the town.

Undoubtedly, I will always cherish hiking in this area. The diverse flora includes tall broadleaf trees such as hickory, beech, oak, birch, and maple, supporting numerous bird species ranging from barred owls to great-crested flycatchers and turkey vultures.

12. Cheshire Park

This public park is situated slightly away from Route 10, near the Southington Town line.

Cheshire Park contains 75 acres, with a quarter dedicated to active recreational facilities, including softball fields, a basketball court, tennis courts, and pickleball courts.

Separate playgrounds cater to children ages 1 to 4 and 5 to 12, along with a pavilion and picnic area. An amphitheater is also available, hosting community events during the summer months.

The less developed areas of Cheshire Park comprise woodlands, accompanied by a small network of trails inviting exploration.

13. Cheshire Hollow Farm

Source: Cheshire Hollow Farm / facebook

This operational farm is located in the picturesque northern region of Cheshire, specializing in the sale of pumpkins and Christmas trees during October and late November, respectively.

Children will particularly enjoy a visit here, as the farm features friendly barnyard animals. During my visit, I encountered miniature horses, pygmy goats, miniature cattle, pot-bellied pigs, rabbits, and chickens.

Some of these animals have been rescued, while others have come from breeders, all raised with the intent of being pets. For instance, one of the pigs would happily follow visitors during their tour.

The farm operates privately outside of designated hours but can be visited pre-arranged, offering a “Family Farm Tour” that lasts approximately 90 minutes for guest interaction with the resident animals.

14. Whippersnapper’s Play Gym

Source: Whippersnapper’s Play Gym / facebook

This indoor recreational facility is designed to facilitate activities that foster self-esteem and confidence among children through play, all within a secure and non-competitive environment.

Children can engage in various explorative and learning opportunities that promote the development of motor skills through games, music, creative movement, and arts and crafts.

A schedule of classes is available, covering yoga, gymnastics, and cheerleading, along with dedicated sessions for toddlers and children with special needs.

During school breaks, special guests from the police and fire departments, aquariums, and farms frequently visit the facility with live animals to enrich the experience.

During the off-summer season, visitors can join Open Play sessions on weekends, priced at $14 per child at the time of publication.

15. Cheshire Strawberry Festival and Craft Fair

Source: Cheshire Strawberry Festival / facebook

Occupying the green in front of the First Congregational Church, the town organizes a strawberry-themed celebration on the second Saturday of June. At the time this article was written, this traditional New England festival was enjoying its ninth decade of celebration.

The event features over 30 curated arts and craft stalls set within a picturesque locale. Live music enhances the ambiance, coupled with numerous activities to engage children, from face painting to bounce houses.

As a strawberry festival, it offers an array of delicious food options, including farm-fresh strawberries served with whipped cream, chocolate-covered strawberries, strawberry shortcake, and strawberry smoothies. For those seeking savory alternatives, traditional favorites such as burgers and hot dogs are also available.