What to do in Cheshire, CT

Activities, attractions and tours

Visit Cheshire

Types of activities

Cheshire travel guide

Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.

Golden sunlight shining on curved Wooden boardwalk over stream near forest

Castle Craig at Hubbard Park, Meriden, CT. American flags in the foreground and an easily replaceable sky.

Fall in New England , photo take on road 70 Cheshire CT

Cheshire Attractions

Let Expedia help you to experience the best that Cheshire has to offer! If you’re planning a trip to Cheshire, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling to Cheshire with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Places of interest in Cheshire

Cheshire is crammed with must-see places to visit and things to do. We can help you decide where to stay in Cheshire, and make it a breeze to explore Cheshire and the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Cheshire to make sure that you enjoy your holiday to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit to Cheshire, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights in Cheshire.

Cheshire attractions

Cheshire has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions in Cheshire to keep you entertained. Expedia makes it easy to book your flight, hotel and rental car in advance, making for hassle-free travel and freeing you up to explore the sights of Cheshire.

Looking for things to do in Cheshire can be time-consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine of Cheshire or catch up with the vibrant local culture, our guides to Cheshire attractions ensure that you’ll have a successful trip, whatever the season. Happy trails!

Explore activities
Explore thousands of experiences from activities and attractions to day tours and transfer.
Book with ease
Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities.
Treat yourself
One Key members save % or more on select activities, hotels, cars and holiday rentals.
Learn about One Key

Recommended things to do in Cheshire

Number of things to do	1
Cheapest thing to do on Expedia	Astonishing University hunt: Yale and Beyond: £12
Top 5 things to do	Astonishing University hunt: Yale and Beyond
Half-day tours	Astonishing University hunt: Yale and Beyond
With kids	Astonishing University hunt: Yale and Beyond

What to do in Cheshire

Popular places to visit

Roaring Brook Park

Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theatre scene.

Barker Character, Comic and Cartoon Museum

You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theatre scene in this romantic area.

Maplecroft Plaza Shopping Center

You can find the perfect gifts to bring home at Maplecroft Plaza Shopping Center during your stay in Cheshire. Experience the area's entertainment venues and theatre scene.

Cheshire Golf Course

Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theatre scene in this romantic area.

Cheshire Hollow Farm

Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theatre scene in this romantic area.

Bartlem Park

Explore the great outdoors at Bartlem Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theatre scene.

Lock 12 Historical Park

Explore the great outdoors at Lock 12 Historical Park, a lovely green space in Cheshire. While in this family-friendly area, you can enjoy the restaurants.

Quinnipiac Recreation Area

Explore the great outdoors at Quinnipiac Recreation Area, a lovely green space in Cheshire. Experience the entertainment venues and theatre scene in this romantic area.

Drazen Orchards

Explore the great outdoors at Drazen Orchards, a lovely green space in Cheshire. Experience the area's entertainment venues and theatre scene.

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

Day trip destinations from Cheshire

Wallingford

Hamden

Frequently asked questions

Is Cheshire worth visiting?

From shopping to outdoor activities and history, there are many great things to do in Cheshire. Don't forget to discover the area's mix of unmissable attractions, local charm and culture.

How do I spend a day in Cheshire?

Lake Compounce and Lake Beseck Beach are two excellent places to kick-start your getaway adventures. Remember to check out the dining and shopping options in Cheshire while you're there too.

What is the top tourist attraction in Cheshire?

Lake Compounce is one of the top tourist attractions in Cheshire and deserves a place on every must-do list of the area.

Is three days enough to stay in Cheshire?

You can easily tour popular sights like Toyota Oakdale Theatre, Sleeping Giant State Park and Mount Southington Ski Area with a three-day stay in Cheshire. On average, many travellers book two days here. There's plenty to see and do nearby too, so stay a bit longer and venture to New Haven.

Is Cheshire a walkable city?

If touring on foot sounds like your kind of getaway, Cheshire is an ideal place to visit. Find major attractions, including Cheshire Hollow Farm, within walking distance of downtown. You can also go for a stroll around Cheshire Historic District, a hip neighbourhood located about 2 kms (1 mile) from downtown.

What are some activities to do in Cheshire with kids?

If you're looking for activities and sights for all the family, have a look at these fabulous ideas for what to do in Cheshire with kids.

Astonishing University hunt: Yale and Beyond

What to do in Cheshire for adults?

There are plenty of things to do in Cheshire, with experiences for adults of all ages. End the day with a visit to Connecticut Law Enforcement Memorial.

Are there free things to do in Cheshire?

In Cheshire, Mount Carmel is a popular spot for anyone looking to enjoy the city without opening their wallet. Also, stroll around the green spaces and other neighbourhoods, and ask a local tour guide for tips. It's a simple way to learn about the best free things to do in Cheshire.