15 Best Things to Do in Cheshire, CT

Cheshire, CT
TAKAZAWA / shutterstock.com

Cheshire may be a small town in Connecticut, but New England's "Bedding Capital" makes it a fascinating travel destination.

The town is filled with vast and gorgeous fields, charming farms, barns, parks, and gardens worth visiting.

Its peaceful ambiance and scenery are a refreshing sight, especially for those who spend most of their time in the concrete jungle.

In addition, Cheshire has fascinating historical sites, adding excitement to your visit there.

Likewise, this small New England town in New Haven County hosts numerous festivals, offering tourists and locals a fun experience every year.

It's also home to some incredible natural attractions awaiting your discovery.

So, pack your bags and read this post on the best things to do in Cheshire, CT.

Hike the Scenic Farmington Canal Heritage Trail

Lock 12 of Farmington Canal Heritage Trail
Staib, CC BY-SA 3.0, via Wikimedia Commons

Outdoor adventure awaits you if you visit the Farmington Canal Heritage Trail upon arrival in Cheshire.

This famous outdoor attraction serves as a state park in Connecticut, which forms a portion of Cheshire and the neighboring town of Hamden.

Many visitors and locals love to hike through its trails or perhaps enjoy other outdoor recreational activities in this state park.

You'll surely satisfy yourself with its hiking trails that run for 17 miles starting from Southington to Hamden.

The hike is relatively easy and enjoyable since the trails feature paved ways, also used for biking, skiing, in-line skating, and jogging.

Hiking through this state park's famous trails is a surefire excellent way to start your Cheshire adventure.

Explore the Barker Character, Comic and Cartoon Museum

It might surprise you that Cheshire is home to an incredible place that features your favorite childhood cartoons and comic book characters.

The Barker Character, Comic, and Cartoon Museum in the Highland Avenue Building is a must-visit place for everyone.

It is a fascinating and unique museum with a vast collection of memorabilia from all famous pop culture characters, including your favorites.

This museum is also a witness to Cheshire's history as it has operated since 1929 through Herbert Barker, a local businessman.

Barker has amassed more than 80,000 toys, wooden cut-outs, board games, lunch boxes, figurines, dispensers, marionettes, playing cards, comic books, and cell art.

So, you'll find rare vintage toys and memorabilia up to the modern ones in the museum exhibits.

While touring, you'll easily spot famous characters like Popeye, Batman, Superman, Mickey Mouse, and the Looney Tunes crew.

Explore the Gorgeous Waterfalls of Roaring Brook Park

The beautiful waterfall of Roaring Brook Park
CamParnoff, CC BY-SA 4.0, via Wikimedia Commons

Cheshire is also home to a gorgeous waterfall you'll find at Roaring Brook Park.

This famous waterfall is the tallest in Connecticut, rising 24 meters from the ground.

A visit to this famous waterfall in Cheshire offers you a splendid experience with nature.

You'll surely enjoy snapping dozens of gorgeous photos with the natural scenery and the waterfalls as your backdrop.

In addition, Roaring Brook is also one of the most famous hiking destinations in New Haven County.

It features red-blazed trails that pass through the waterfalls and numerous lush-green forested areas, including the Quinnipiac Blue Trail.

So, pack your hiking boots for your Cheshire adventure because you'll find yourself traversing this gorgeous park sooner rather than later.

Celebrate the Cheshire Strawberry Festival and Craft Fair

Every June, everyone in Cheshire gets out to the streets to celebrate the annual Cheshire Strawberry Festival and Craft Fair.

The annual festival has taken place in the town for more than 80 years.

It continues to grow bigger and become more exciting each year.

Over 30 artists and craftspeople gather during the festival to showcase their latest masterpieces.

At the same time, you can enjoy various music, food, entertainment, and other attractions during the festival.

Of course, since it's a strawberry festival, you can expect lots of delicious strawberry dishes and pastries.

So, visit Cheshire in June to witness this New England traditional festival giving color and fun to many people.

Stroll through the Cheshire Historic District

Exterior of First Congregational Church at Cheshire Historic District
John Phelan, CC BY-SA 3.0, via Wikimedia Commons

Cheshire's downtown area, or what locals call the historic district, is a sight to behold.

The town's historic district is south of Main Street's junction and Academy Road.

Cheshire Historic District is an excellent example of what New England's beautiful rural towns looked like back in the day.

One of the most distinctive historical sites you'll likely visit is the 1827 First Congregational Church of Cheshire.

Also, you'll come across the Greek Revival Town Hall, constructed in 1867, and many more historical houses and buildings.

The Cheshire Historic District covers 35 acres, mostly filled with green open spaces and early 1800s and mid-1900s structures.

Taking a stroll at this place in Cheshire is both nostalgic and mesmerizing.

You'll pass through centuries-old structures such as Victorian houses, period buildings, charming shops, cafes, and businesses.

Have Fun at the Bartlem Recreation Area

If you're up for some fun-filled sports activity or perhaps a simple workout, head to Cheshire's go-to place, the Bartlem Recreation Area.

This well-equipped recreation area in Cheshire is situated just across from Cheshire High School.

The Bartlem Recreation Area has a 90-foot baseball diamond, a lacrosse field, soccer field, skate park, community pool, and a unique playground.

During winter, the recreation area becomes another winter sports park.

One of its most distinct winter sports facilities is the Greg Schena Memorial Ice Skating Rink.

One of the best reasons you and your loved ones need to visit the Bartlem Recreation Area is that there is no entry fee.

It is open to everyone who wishes to use its sports facilities.

Likewise, picnicking and sightseeing are also popular activities here.

Buy Fresh Produce at the Cheshire Farmers' Market

Do you want to taste local pastries, home-cooked meals, or perhaps buy fresh produce in Cheshire?

Then head to the Cheshire Farmers' Market situated outside Chester Town Hall.

It's the best place in Cheshire to enjoy delicious food and drinks.

At the same time, you'll also enjoy selecting a vast array of fruits and vegetables freshly harvested from local farms in the region.

It's an incredible place to visit if you're yearning to immerse yourself in the Cheshire community.

This farmers' market is exciting because it regularly hosts food festivals, concerts, cookouts, and wine events.

With that in mind, it is unique among the farmers' markets you might have visited already.

More than 25 local Cheshire businesses and companies gather at the farmers' market, displaying their best products.

So, spend your mornings at Cheshire Farmers' Market and enjoy its unique experience with the locals.

Learn Fascinating History with the Cheshire Historical Society

Exterior of Cheshire Historical Society
Magicpiano, CC BY-SA 4.0, via Wikimedia Commons

The Cheshire Historical Society is housed in a historical building, the Hitchcock-Phillips House, constructed in 1785.

This house is adjacent to another famous historical attraction in Cheshire, the First Congregational Church.

If Cheshire's history and heritage fascinate you, head to the Cheshire Historical Society, the town's local museum.

Visiting the Cheshire Historical Society lets you appreciate how the townsfolk lived back in the day.

Check out its exhibits displaying period fittings, artworks, old firearms, and household items.

Celebrate the Holidays at Cheshire Hollow Farm

Whether you're visiting Cheshire on Halloween or Christmas, Cheshire Hollow Farm offers something exciting for everyone.

This working farm in Cheshire is an excellent place to visit during the Holidays because of its pumpkins and Christmas trees harvested during these seasons.

Aside from buying pumpkins at the Cheshire Hollow Farm, you and your loved ones will surely enjoy fun farm activities.

You and your loved ones will enjoy feeding farm animals such as miniature horses, miniature cattle, pygmy goats, pot-bellied pigs, bunnies, and chickens.

Of course, your visit there won't be complete without buying its signature Christmas trees or Halloween pumpkins as souvenirs.

Pick Fruits at Drazen Orchards

Cheshire is home to a charming fruit farm known as the Drazen Orchards, where you can enjoy fruit-picking with your loved ones.

This orchard in Cheshire has been in business since the 1950s, making it one of the longest-running orchards in the county.

Today, it's a famous attraction in Cheshire which lets visitors experience fruit-picking through its vast orchards, featuring dozens of fruits.

Drazen Orchard lets visitors pick plums, blueberries, nectarines, quinces, peaches, and pears.

In addition, Drazen Orchards has 14 apple varieties which you can also pick during your visit there.

After a tiring harvest, you can proceed to its shop and enjoy apple cider donuts, pies, and cider.

Other Things to Do Nearby

Visit the Castle Craig Tower

Exterior of Castle Craig Tower
MSaucier / Shutterstock.com

Cheshire is home to remarkable ruins likened to a Medieval fortress, the Castle Craig Tower.

This historical landmark is in Hubbard Park, atop Hanging Hills' eastern peak.

You can find it in Meriden, 25 minutes from Cheshire.

Many visitors describe this historical attraction as a forgotten fortress now in ruins.

Close details of Castle Craig Tower
ARENA Creative / Shutterstock.com

Historically, Castle Craig served as an observation tower in Meriden, standing 33 feet high and having a base of 59 feet.

In 1900, Walter Hubbard had the tower built as a gift to the people of Meriden.

Visiting this attraction is like seeing a Medieval tower usually found in Europe and England.

Reconnect with Nature at Mount Sanford

Drive southwest of Cheshire to reach the spacious environs of Mount Sanford, which is part of the Naugatuck State Forest.

You can start your journey from Bethany, Connecticut, ten minutes from Cheshire.

The entire state forest spans 4,153 acres, covering eight towns, including Cheshire.

Mount Sanford serves as one of Naugatuck State Forest's focal points.

Many hikers and climbers frequently hike to its 270-meter peak that overlooks vast state forest areas.

Before returning home, embark on one last round of hiking at Mount Sanford to treat yourself or your loved ones to a worthwhile experience.

Wander the Sleeping Giant State Park

Welcome sign of Sleeping Giant State Park
Kenneth C. Zirkel, CC BY-SA 4.0, via Wikimedia Commons

Go south of Cheshire to arrive at a fascinating natural attraction, the Sleeping Giant State Park.

This park is in Hamden, Connecticut, 11 minutes from Cheshire.

You can find it on the southern portion of the Quinnipiac Trail and Metacomet Ridge.

It's best known for the massive protruding figure distinctly shaped like a person lying down.

Sleeping Giant State Park is more than just its unique rock formations and landscape.

The tower of Sleeping Giant State Park
Aubrey Gough / Shutterstock.com

It's also a famous hiking destination, wherein hikers can enjoy more than 30 miles of scenic trails in the wilderness of New Haven County.

Aside from hiking, you can climb the 120-meter cliff, which is the sleeping giant's head.

At the same time, you can climb further at the sleeping giant's hip, which takes you another 225 meters, which is the highest point in the area.

To complete your climb, you can scale an observation tower where you'll enjoy a magnificent 360-degree view of the entire park.

Scenic sunset at Sleeping Giant State Park
Britney Beardsley / Shutterstock.com

Discover the Vast Wilderness of Hubbard Park

For outdoor adventurers, Hubbard Park is a terrific place to visit.

You can find it in Meriden, Connecticut, 15 minutes from Cheshire.

Hubbard Park highlights mountainous wilderness mixed with landscaped areas.

In the early 20th century, wealthy Meriden industrialist Walter Hubbard donated 1,800 acres of unspoiled natural area to the city for use as a park.

One of the most distinct attractions in the park is the Hanging Hills, a prehistoric basalt formation at the Metacomet Ridge.

This 200-million-year-old rock formation is a famous place that people frequently visit to snap gorgeous photos of the natural scenery.

In addition, Hubbard Park is famous for its trails excellent for hiking, cross-country skiing, and cycling.

Every April, it's where the annual Meriden Daffodil Festival takes place.

Thousands of people across New England gather to enjoy rides, crafts, arts, food, and fireworks to celebrate the blooming of 600,000 daffodils.

Hike the Quinnipiac Trail

For another worthwhile hiking trip in Cheshire, head to the Quinnipiac Trail that meanders through Mill River.

It's also in Meriden, 12 minutes from Cheshire.

The Quinnipiac Trail stretches 24 miles through Cheshire and connects the Blue-Blazed Trail.

You'll pass through gorgeous natural sceneries and awe-inspiring landmarks around town.

Many hikers who have walked this trail have described it as relatively easy and scenic.

Quinnipiac Trail comprises gentle woodland, and you'll pass a ridge that carries you to numerous basalt formations in Roaring Brook Falls.

Overall, it's a worthwhile hiking experience in Cheshire that you shouldn't miss.

Final Thoughts

Cheshire is a short drive from New Haven and Connecticut's other coastal cities and towns, making it conveniently accessible for those planning to visit.

Most importantly, Cheshire is worth exploring because of its magnificent landscape and sceneries, showcasing the signature New England charm.

Start planning your Cheshire trip today!

Spotted a mistake, have some feedback, or just want to chat with our editorial team? Click here to get in touch.
Find out more about Travel Lens and read our editorial guidelines here.