One of their most unique and most visited attractions in Cheshire, CT is the Barker Character Comic and Cartoon Museum which is sure to make you nostalgic for your childhood. Explore the area’s vast outdoors by going apple picking at the Drazen Orchards or attending the Daffodil Festival at Hubbard Park.

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1.Barker Character Comic and Cartoon Museum

Barker Character Comic and Cartoon Museum
© Barker Character Comic and Cartoon Museum

A must-visit attraction for visitors of all ages and those who are children at heart, the Barker Character Comic and Cartoon Museum guaranteed to be a fun and memorable experience. There are over 80,000 items on display in the museum, which means that you can spend hours looking through all of the collector’s items and memorabilia. Some of their greatest features are the array of lunch boxes you’ll find neatly hanging from the ceiling, one of the largest toy collections in the nation, and even McDonald’s Happy Meal toys. What’s great is that visitors old and young will find something they relate to as characters such as Felix the Cat all the way to Kim Possible ignite childhood memories.

1188 Highland Avenue, Building B, Cheshire, CT 06410, Phone: 203-699-3822

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2.Drazen Orchards

Drazen Orchards
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The history of Drazen Orchards dates all the way back to the early 1800s when it started as an orchard, farm, and wood mill. The Drazen family came upon it in the 1950s and soon implemented an Integrated Pest Management method which helps the fruits grow as naturally as possible. The orchard has many varieties of apples such as Honeycrisp, Zestar, and Cortland; other fruits also include blueberries, peaches, pears, and plums. You can head over to the Farm Stand, which is open seasonally, and purchase from a wide array of freshly picked fruits and vegetables that are grown right there on the orchard. Bring the family along and pick your own as it’s a wonderful experience for people of all ages.

251 Wallingford Road, Cheshire, CT 06410, Phone: 203-272-7985

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3.Cheshire Historical Society

Cheshire Historical Society
© Cheshire Historical Society

Visiting the Cheshire Historical Society is the best way to better understand and appreciate the town’s history which is kept alive through the museum’s exhibitions, collections, and programs. You’ll see a number of artifacts and memorabilia which reflect the people that lived there and the events that have taken place over time. Their events are incomparable; for example, the Christmas Holiday Open House is a lovely Georgian-themed holiday party that everyone is invited to. The society is currently located at the Hitchcock - Phillips House, which on its own is filled with a history and charm that can’t be experienced elsewhere.

43 Church Drive, Cheshire, CT 06410, Phone: 203-272-2574

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4.Cheshire Hollow Farm

Cheshire Hollow Farm
© Cheshire Hollow Farm


Cheshire Hollow Farm is a year-round, fully operational farm that is home to a variety of animals such as pygmy goats, miniature cattle, miniature horses, chickens, pot-bellied pigs, and bunnies. The tours are a great way to meet the farm animals, pet and feed them, and learn about how they live on the farm. The farm sits on over a hundred acres of gorgeous land that is just perfect for exploring - there’s always a nature hike or scavenger hunt scheduled at the farm. Their seasonal offerings are so much fun; if you find yourself there during the summer, go on a scheduled tour or sign the kids up for a summer camp session. During Autumn and Winter, you can go pumpkin picking, enjoy hay rides, and purchase the perfect Christmas tree.

1559 Peck Lane, Cheshire, CT 06410, Phone: 203-500-9288

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5.Whippersnapper's Play Gym

Whippersnapper's Play Gym
© Whippersnapper's Play Gym


Whippersnapper’s Play Gym is an indoor play area that allows children to have fun in a safe environment while participating in extraordinary programs and unique activities which help develop their self-esteem and confidence. The innovative gym gives children the opportunity to explore creative movement, music, games, fitness, and arts and crafts, while developing fine and gross motor development skills. In addition to the skill development classes, they also offer workshops on yoga, cheerleading, and gymnastics. There’re specific classes for toddlers, older children, and children with special needs, ensuring that children of all ages and on all levels have a fabulous time at Whippersnapper’s.

360 Sandbank Road, Cheshire, CT 06410, Phone: 203-272-4386

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6.Hubbard Park

Hubbard Park
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Listed on the U.S. National Register of Historic Places, Hubbard Park spans over 1,800 acres and is filled with things you can see and do. Hike through the park and take in its beautifully-maintained woodlands, cliffs, streams, lakes, and flower gardens. Pack a picnic and enjoy some time with friends and family beside the stunning Mirror Lake or on one of the many designated picnic spots. In addition to hiking, there are trails on which you can enjoy bicycling, mountain biking, and backcountry skiing. The park is the site of several local festivals and concerts including the most notable, the Daffodil Festival, which has a parade and fireworks.

999 W Main Street, Meriden, CT 06451

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7.Sleeping Giant State Park

Sleeping Giant State Park
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Sleeping Giant State Park is home to the namesake Sleeping Giant which is popularly known as Mount Carmel. The rugged traprock mountain is a prominent landscape feature and can be seen from miles around; the towering structure resembles a slumbering human and is a magnificent sight to see. Activities that you can partake in while at the park including rock climbing, hiking, bird watching, picnicking, horseback riding, snowshoeing, and cross-country skiing. Visitors can also go fishing on Mill River or camping in designated areas that are filled with restrooms and picnic shelters. The state park is open year round so if you’re in the area, be sure to stop by and explore.

200 Mount Carmel Avenue, Hamden, CT 06518, Phone: 203-287-5658

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8.Viron Rondo Osteria

Viron Rondo Osteria
© Viron Rondo Osteria

Osteria is an Italian word that translates to a place which serves simple, yet delicious, food and wine, and at Viron Rondo Osteria you are guaranteed mouthwatering cuisine made from fresh, simple ingredients. Their seasonal menu is sure to tantalize your taste buds and includes everything from the perfect thin crust pizza to several well known and loved Italian classics. The homemade pasta such as the fettucine carbonara or the lasagna are a few of the must-try entrees offered. Other popular entrees also include the apple cider braised short ribs, the black pearl organic salmon, chicken marsala, and the calamari fra diavolo which is tossed in a spicy plum tomato sauce.

1721 Highland Avenue, Cheshire, CT 06410, Phone: 203-439-2727

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9.Watch Factory Restaurant

Watch Factory Restaurant
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If you’re looking for an amazing and incomparable food experience then feast on delicious Austrian country cuisine at the Watch Factory Restaurant. The restaurant is filled with old-world charm and has a unique setting that makes for a lunch or dinner experience that isn’t available anywhere else. It has gotten amazing reviews from establishments such as The New York Times, Connecticut Magazine, TripAdvisor, and their most wonderful critics, their loyal patrons. Come and enjoy delicious plates of mussels in mustard cream, marinated beets and gorgonzola, black pearl salmon with tomato herbed cream, and their rack of lamb with red wine and parsley.

122 Elm Street, Cheshire, CT 06410, Phone: 203-271-1717

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10.Blackie's Hot Dog Stand

Blackie's Hot Dog Stand
© Blackie's Hot Dog Stand

Blackie’s Hot Dog Stand is a community staple and has been a Connecticut tradition ever since it first opened in 1928. You will find the delicious hot dogs made from the original recipes along with their homemade relish - it may all seem simple, but once you try it no other hot dog will ever taste the same again. The famous Blackie relish is what really brings it all together; the secret family recipe is unlike any other relish, combining both sweet and spicy. The stand stays true to tradition, only offering their hot dogs, relish, birch beer on tap, cartons of chocolate milk, and continuing to close on Fridays.

2200 Waterbury Road, Cheshire, CT 06410, Phone: 203-699-1819

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10 Best Things to Do in Cheshire, Connecticut