Things to Do in Cheshire Connecticut

Enjoy the Great Outdoors at Sleeping Giant State Park

Sleeping Giant State Park is one of the most popular outdoor destinations in Cheshire, Connecticut.

With its iconic two-mile-long mountaintop resembling a giant lying in repose, this park offers vibrant outdoor opportunities through all seasons.

The park is home to over 30 miles of hiking trails that vary in difficulty from easy to strenuous.

For new visitors, the Tower Trail is a must, leading hikers up a 1.6-mile route to a stone tower with panoramic views of the surrounding areas.

Pack a picnic and enjoy a leisurely afternoon in one of the many picnic areas available.

On a sunny day, you might spot families playing games, couples enjoying a scenic walk, or runners challenging themselves on the rugged trails.

Step Back in Time at the Barker Character, Comic and Cartoon Museum

The Barker Character, Comic and Cartoon Museum is a hidden gem for fans of pop culture and vintage memorabilia.

Home to a collection of over 80,000 items, the museum showcases toys, lunch boxes, advertising memorabilia, and more, dating back to the late 1800s.

Kids and adults alike will enjoy seeing their favorite characters from yesteryear and reminiscing about the past.

The museum offers a fascinating insight into the evolution of American pop culture.

If you’re planning a visit, check their schedule for any special exhibitions that might be on display during your visit.

Indulge in Local Flavors at The Watch Factory Restaurant

For an exceptional dining experience, make your way to The Watch Factory Restaurant.

This historic venue, once an actual watch factory, now serves as a charming restaurant with a unique ambiance.

Their menu boasts a variety of delicious dishes, from fresh seafood to succulent steaks, all prepared with locally sourced ingredients.

Don’t miss out on their signature cocktails and wide selection of wines.

It’s a perfect spot for a romantic dinner or a special family celebration.

Reservations are recommended, especially on weekends.

Explore Nature at Roaring Brook Falls

If you’re a nature enthusiast, Roaring Brook Falls is a must-see.

This picturesque waterfall offers a tranquil escape from the hustle and bustle of everyday life.

The hike to the falls is relatively short but rewarding, with breathtaking views along the way.

Autumn is an especially beautiful time to visit, with the surrounding foliage in full display.

Weekends can be busy, so consider visiting during the week for a more peaceful experience.

Pick Your Own at Drazen Orchards

Drazen Orchards is a family-owned farm that offers a delightful pick-your-own experience.

Depending on the season, you can pick apples, peaches, or pumpkins.

The orchard also sells fresh cider, baked goods, and seasonal decorations.

It’s a perfect outing for families with children, offering a fun and educational experience.

Make sure to check their website for picking schedules and special events.

Visit the Cheshire Historical Society

Learn about the rich history of Cheshire at the Cheshire Historical Society.

Located in the charming Hitchcock-Phillips House, the society offers a glimpse into the town’s past through various exhibits and artifacts.

You might find exhibits on everything from colonial-era life to local industries that shaped the town.

They also host special events and lectures throughout the year, providing deeper insights into local history.

Admission is free, but donations are welcome.

If you’re interested in exploring more historical sites, you might also enjoy visiting some historical landmarks in the nearby Rhode Island area.

Enjoy a Day on the Farm at Norton Brothers Fruit Farm

Norton Brothers Fruit Farm is a fun and educational outing, perfect for families and individuals alike.

You can pick your own fruits, shop for fresh produce, or simply enjoy the scenic views of the farm landscape.

The farm stand offers freshly picked fruits, homemade jams, and other farm products.

During the fall season, it’s a popular spot for apple picking and enjoying fresh apple cider.

Weekends can get busy, so visiting on a weekday is a great way to enjoy a quieter experience.

Get Active at Cheshire Park

Cheshire Park is a community hub offering various activities for people of all ages.

With playgrounds, sports fields, and walking trails, it’s a great place to spend a day outdoors.

The park also hosts community events and sports leagues, providing ample opportunities for social interaction and physical activity.

If you enjoy hiking, you might find it interesting to compare the trails here with some of the best trails in Rhode Island.

Whether you’re looking to join a pick-up game of soccer, enjoy a picnic, or take a leisurely walk, Cheshire Park has something for everyone.

Relax with a Spa Day at Serenity Now Massage & Wellness

If you’re in need of some pampering, Serenity Now Massage & Wellness is the place to go.

They offer a variety of services, including massages, facials, and holistic treatments.

Customers rave about the serene atmosphere and skilled practitioners.

Booking a session here is a great way to unwind and rejuvenate your mind and body.

If you’re here for multiple days, you might also want to consider staying at one of the premier hotels not too far from Connecticut for a complete relaxation experience.

Shop at Maplecroft Plaza

For a bit of retail therapy, head over to Maplecroft Plaza.

This shopping destination features a variety of stores, from clothing boutiques to specialty shops.

It’s a great place to pick up a unique gift or treat yourself to something special.

Don’t miss the seasonal sales and special promotions, which can offer significant savings.

After a day of shopping, you can dine at one of the nearby restaurants that offer excellent dining options.

Experience Local Culture at Artsplace

Artsplace is the go-to spot for anyone with a passion for the arts.

This community art center offers classes and workshops in various disciplines, including painting, pottery, and more.

It’s a great way to explore your creative side or try something new.

The center also hosts art exhibitions and special events, providing a platform for local artists to showcase their work.

Be sure to check their schedule for upcoming classes and events that might interest you.

Attend the Cheshire Fall Festival

One of the highlights of the year in Cheshire is the annual Cheshire Fall Festival.

This community event features live music, food vendors, craft stalls, and more.

It’s a great opportunity to enjoy local entertainment and sample delicious treats from various vendors.

The festival typically takes place in September and is a fun outing for families, friends, and visitors of all ages.

Mark your calendar and don’t miss out on this community-driven celebration.

Plan a Visit to Cheshire Hollow Farm

Cheshire Hollow Farm is a charming family-owned farm that offers a variety of activities for visitors.

You can meet farm animals, enjoy a hayride, or simply take in the beautiful scenery.

The farm also hosts seasonal events, such as pumpkin picking in the fall and farm-to-table dinners in the summer.

It’s a wonderful place to experience the rural charm of Connecticut and spend quality time with loved ones.

Have Fun at Cheshire Bowl

For a bit of indoor fun, head over to Cheshire Bowl, a popular bowling alley that offers hours of entertainment.

The facility features multiple lanes, an arcade, and a snack bar, making it a perfect spot for family outings or a night out with friends.

Check their website for special deals and league information if you’re interested in joining a team.

Discover Literature at Cheshire Public Library

The Cheshire Public Library is more than just a place to borrow books; it offers a wealth of resources and activities catering to all age groups.

The library has a robust collection, including books, audiobooks, and digital resources, making it an intellectual haven for readers and learners.

Throughout the week, the library hosts various programs such as story time for children, book clubs for adults, and technology workshops.

If you’re interested in expanding your digital knowledge, the library also offers free access to online courses and computer classes.

Be sure to check their calendar for special events like author visits, craft workshops, and film screenings.

Joining the library’s community events can be a delightful way to meet new people and engage with other literate enthusiasts.

Explore Art at the Ball & Socket Arts

Ball & Socket Arts is a unique cultural initiative converting a historic factory into a vibrant cultural center.

Once completed, it will feature art galleries, performance spaces, and art studios, bringing a creative hub to Cheshire.

The project aims to support local artists and offer a variety of programming to educate and bring the community together through the arts.

Currently, you can participate in pop-up events that give a sneak peek into what’s in store for the future.

Whether it’s watching a performance or viewing an art installation, Ball & Socket Arts promises a unique cultural experience.

Keep an eye on their website for upcoming events and opportunities to engage with their artsy endeavors.

Enjoy Farm-to-Table Dining at Viron Rondo Osteria

For a dining experience that emphasizes fresh, local ingredients, Viron Rondo Osteria is a must-visit.

This restaurant offers a farm-to-table menu that changes with the seasons, ensuring the freshest flavors in every dish.

Their menu includes a variety of Italian-inspired dishes, from handmade pasta to wood-fired pizzas and delectable desserts.

The ambiance is warm and inviting, making it a great spot for both casual meals and special occasions.

There’s also an extensive wine list to complement your meal, much to the delight of wine aficionados.

Given its popularity, reservations are highly recommended, particularly on weekends and holidays.

Play Sports at Cheshire Community Pool

The Cheshire Community Pool is a fantastic facility for those looking to stay active and healthy.

The indoor aquatic center features a large pool suitable for lap swimming, water aerobics, and family swim times.

It’s an excellent venue for kids’ swim lessons and water fitness classes for adults.

The pool also hosts swim teams and competitions, attracting swimmers from all over the area.

Memberships and day passes are available, offering flexible options whether you’re a local resident or just visiting.

It’s best to check their schedule online to find the perfect time for your preferred activities without the crowds.

If swimming isn’t your thing, you might also enjoy some other scenic waterfront spots that offer a relaxing day out.

Taste Unique Treats at Sweet Claude’s Ice Cream

Satisfy your sweet tooth at Sweet Claude’s Ice Cream, a beloved local ice cream parlor that has been serving up smiles for years.

Offering a wide range of homemade ice creams, sundaes, and milkshakes, Sweet Claude’s is a hit with locals and visitors alike.

Customers rave about their rich, creamy flavors and the store’s nostalgic, friendly atmosphere.

Seasonal flavors and creative concoctions make every visit a new experience.

If you’re visiting during the warmer months, enjoy your cone outside on their charming patio area.

It’s the perfect stop after a day of exploring Cheshire or as a treat to cool off during summer adventures.

Appreciate History at The Lock 12 Historical Park

The Lock 12 Historical Park offers a fascinating glimpse into Cheshire’s history and the bygone era of canal transportation.

The park features a restored 19th-century canal lock and a small museum where you can learn about the canal’s history.

The scenic park setting is a lovely spot for a leisurely stroll, a picnic, or some quiet reflection near the water.

Children and history buffs alike will enjoy the educational plaques that detail the canal’s operation and significance.

Special events and guided tours are available, often led by enthusiastic local historians.

This tranquil spot is a great educational outing for families and a peaceful retreat for solo visitors.

Shop Local at Cheshire Farmers Market

For fresh produce and artisan goods, the Cheshire Farmers Market is the place to be.

This local market runs seasonally and features farmers, bakers, and artisans from across the region.

You’ll find everything from fresh vegetables and fruits to handmade crafts and baked goods.

Supporting local vendors means you’re also supporting the Cheshire community, making it a feel-good shopping experience.

It’s an enjoyable way to spend a morning, perusing stalls, sampling foods, and chatting with the vendors.

Don’t forget to bring your reusable bags and perhaps a small cooler for perishables.

Markets like these often have hidden gems similar to the farmers markets found in Rhode Island.

Stay Fit at the Cheshire Fitness Zone

The Cheshire Fitness Zone is an excellent place to maintain or kickstart your fitness routine.

This full-service gym offers a variety of classes, personal training options, and modern gym equipment.

Whether you’re a fitness veteran or just beginning, the friendly staff can help tailor a workout plan that suits your goals.

Classes range from high-intensity interval training (HIIT) to yoga and pilates, catering to various fitness levels and interests.

Membership packages vary, allowing you to choose what best fits your schedule and commitment level.

Check their class schedule online to find something that excites and motivates you to stay active.

Get Creative at the Cheshire Performing Arts Center

If performing arts are your passion, the Cheshire Performing Arts Center offers numerous opportunities.

From theater productions to dance recitals, there’s always something exciting happening at the center.

They offer classes and workshops in acting, dance, and music, welcoming participants of all ages and skill levels.

The center is also home to community theater groups, making it a lively hub for creative talents in Cheshire.

Audience members will enjoy high-quality performances in a comfortable and inviting setting.

Keep an eye on their event calendar for upcoming shows and enroll in classes to explore your artistic abilities.

Enjoy a Movie Night at Bartlem Park

Bartlem Park is more than just a typical park; it often hosts community events like outdoor movie nights.

These events are perfect for families looking to enjoy a movie under the stars.

Bring a blanket and some snacks, and enjoy classics and new releases in a family-friendly atmosphere.

The park also has playgrounds and sports facilities that can be enjoyed before the movie starts.

Check the town’s website for schedules and movie listings so you can plan your visit accordingly.

Get Lost in Literature at Books & Company

For book lovers, Books & Company is an independent bookstore offering a curated selection of books and unique gifts.

The cozy atmosphere makes it a welcoming place to browse and find your next great read.

The store often hosts author signings, book clubs, and reading events, creating a community hub for literary enthusiasts.

Don’t miss their seasonal sales for excellent deals on your favorite titles.

If you love diving into a good book, this store is a must-visit.

Dine at Pop’s Pizza

Pop’s Pizza is a beloved local eatery known for its delicious pizzas and welcoming atmosphere.

Using fresh ingredients and traditional recipes, Pop’s Pizza offers everything from classic margherita to innovative specialty pizzas.

Many Cheshire residents rave about the friendly service and cozy environment.

If you’re visiting, this spot is perfect for a casual meal with family or friends.

Don’t forget to try their popular garlic knots, a local favorite.

Explore the Cheshire Trail

The Cheshire Trail is perfect for outdoor enthusiasts who enjoy walking, jogging, or biking.

This trail offers scenic views and a peaceful escape from the hustle and bustle of daily life.

The trail is well-maintained and easily accessible, making it suitable for all ages and fitness levels.

It’s a fantastic place to get some exercise and enjoy the natural beauty of Cheshire.

Consider visiting during the early morning or late afternoon to avoid crowds and enjoy a quieter experience.

Connect with Nature at Ives Farm

Ives Farm is a working farm that offers opportunities to connect with nature and learn about agriculture.

Visitors can purchase fresh produce, explore walking trails, and take part in educational programs.

Seasonal events such as harvest festivals and guided tours provide even more reasons to stop by.

The farm emphasizes sustainable practices, making it a great place to learn about eco-friendly farming.

It’s a wonderful outing for families wanting to experience farm life firsthand.

Stay Active at the Cheshire Dog Park

For dog owners, the Cheshire Dog Park is the go-to spot for exercising and socializing your furry friend.

This fenced park provides a safe and fun environment for dogs to run and play off-leash.

The park has separate areas for small and large dogs, ensuring a comfortable experience for all.

Regular visitors appreciate the clean facilities and friendly community atmosphere.

It’s a fantastic venue to let your dog burn off some energy while you enjoy the company of fellow dog lovers.

Visit the Cheshire Craft Brewery

The Cheshire Craft Brewery offers a delightful experience for beer enthusiasts.

Featuring a variety of locally brewed beers, the brewery provides a cozy setting for tasting and socializing.

Regularly changing brews ensure that there’s always something new to try.

The brewery often hosts events like beer tastings and live music nights, making it a lively spot to enjoy.

If you’re a fan of craft beer, this brewery should be on your list of places to visit in Cheshire.

Pair your visit with some snacks or food from nearby eateries for a complete experience.

Unwind at the Winding River Antiques

Winding River Antiques is the perfect place for those who love to hunt for unique finds and vintage treasures.

This charming antique store offers a vast array of items, from furniture to collectibles.

Browsing through the eclectic collections can be a fun and relaxing way to spend an afternoon.

With new items arriving regularly, each visit can be a new adventure.

It’s an ideal spot for finding one-of-a-kind gifts or adding something special to your home.

Adventure at Ravine Park

Ravine Park is a fantastic location for outdoor adventure and exploration.

With its rugged terrain and beautiful landscapes, the park is a favorite among hikers and nature lovers.

The trails offer varying levels of difficulty, catering to both beginners and experienced hikers.

Wildlife sightings are common, adding an element of excitement to your hike.

It’s an excellent spot to enjoy the natural beauty of Cheshire and get some exercise.

Engage in Community Events

Cheshire hosts a variety of community events throughout the year that bring people together and celebrate local culture.

From farmers markets and craft fairs to holiday parades and concerts, there’s always something happening in town.

These events provide excellent opportunities to meet locals and experience the community spirit of Cheshire.

Be sure to check the town’s event calendar for upcoming activities and join in the fun.

Whether you’re a resident or a visitor, these events are a great way to feel a part of the community.