5 Connecticut Small Towns to Explore with Kids Last Updated: August 2022

CTvisit.com is proud to partner with some of Connecticut’s most popular bloggers for ideas, insights and inspirations from the people who are lucky enough to call Connecticut home. This CT Ambassadors article is from our friends at Mommy Poppins Connecticut

Cities like New York and Boston can be fun, but just a short drive to Connecticut and you'll find 169 inviting towns that dot the countryside, hills, and coastline. Whether you’re looking for outdoor adventures, wonderful museums with fun family programing, or just strolling charming town centers, browsing the shops and enjoying great food, you can find it all in these small towns in Connecticut. 

Exploring in Kent

Hike around Kent Falls and enjoy stunning views. (Above)

If you ever want to feel like a Gilmore Girl (and who doesn’t?), then Kent is for you! This quintessential town is a prime example of the charm of Litchfield County. Beautiful countryside (check), charming village (check) packed calendar of seasonal festivals (check, check, and check!) Perhaps the most “Kent” thing to do is take a hike up Kent Falls and enjoy a picnic. While you're there, hop on a ride with the Bicycle Tour Company, which offers rentals and cycling excursions for all levels.

Boat Ride in Branford

Search for pirate's treasure in the Thimble Islands.

This shoreline community is one of our favorite Connecticut staycation destinations. We call it the “Bike, Brews, and Views” day trip.  You can’t get much more “Connecticut” than family friendly breweries, stunning coastal landscape, pirates, and lobster rolls. Start the day with a leisurely cruise around the archipelago known as the Thimble Islands. Then take a bike ride along the Shoreline Greenway Trail and take in some stunning scenery. We then end our day at the Stony Creek Brewery – but make sure you stop at the Lobster Shack first to grab a lobster roll to-go (Connecticut style, of course!) 

Flower Picking in Essex

Cut some farm-fresh flowers at Scotts Farm & Greenhouses.

It would be impossible to create this list without mentioning Essex, after all it was rated the “Best Small Town in America.” Expect winding roads, historic homes, vintage steam trains, a fantastic museum, and antiques shops. Yes, Essex is all that and it has a family friendly tap room with regular sing-a-longs.  The Griswold Inn & Tap Room is one of the oldest continuously operating inns in the country, and its nightly schedule of live music should not be missed!  In the summer, we also like to pick flowers from Scott's Farm & Greenhouses. Visitors are given clippers and a basket to fill with fresh fragrant blooms. Make sure you bring a bucket of water so these beauties will survive the trip home.

Meet a Whale in Mystic

Get up close and personal with beluga whales at Mystic Aquarium. 

Come for the Aquarium Seaport, stay for the charm. Mystic is perhaps one of the most visited locations in the state, but that doesn’t mean it lacks small town charm. In the summer, visitors swarm the streets for pizza and beluga whales, but this town is a true gem.  If your kids don’t get the whole pizza Mystic Pizza thing, just take them to Mystic Drawbridge Ice Cream, watch the kayakers and boats float by, and reminisce about simpler times. 

Strolling in Simsbury

Enjoy a walk down the Simsbury Art Trail. 

Located about 15 miles west of Hartford, charming would aptly describe Simsbury. You can enjoy a walk around town on the Simsbury Art Trail, bike through Stratton Brook State Park, or enjoy a haunted burger at Abigail’s Grill. Don't miss the friendly farm folk at Flamig Farm too. You can’t get much more small town than that! 

Mommy Poppins Connecticut

Mommy Poppins Connecticut is a blog devoted to moms and kids on the go. Visit the site or sign up for their free weekly newsletter and let the adventure begin! Photo Credits: Mommy Poppins, The Seward Johnson Atelier, Inc.