Indigenous Peoples Day Weekend 2025 includes celebrations of culture and family fun in CT. Photo courtesy of the Mystic Seaport Museum

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By land, by sea, by river—however!— families are coming to the best Museums in Connecticut! Connecticut River Museum photo by Ally Noel for Mommy Poppins

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Hop aboard for a trip through Litchfield County and fun things to do with kids! Naugatuck Railroad photo courtesy of the Railroad Museum of New England.

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Costumed interpreters share stories of colonial life along the historic Mystic seaport. Photo courtesy of the Mystic Seaport Museum

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Bike the ground of Fort Trumbull. Photo courtesy Visit CT

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Weekend Fun: County Fairs, Insane Inflatable, Lighted Boat Parade

Catch the final weekend of the Orange County Fair in Middletown. Photo courtesy of the fair

7/24/19 - By Susan Miele

A bounty of festivals and other summer fun continues this weekend for Westchester and Hudson Valley families.

Held in a rural setting, the second annual Hudson Valley Brassroots Festival offers two days of brass-band music, plus food, farm tours, and a kids’ processional.

The Putnam County Fair has all the trappings of carnival amusement, live animals, and other fun stuff. If your family likes action, you won’t want to miss the Insane Inflatable 5K—not your toddler’s bouncy house, for sure, though there are kid-directed options.

Other top picks: For daytime fun, the Stony Kill Butterfly Festival; for evening fun, watch the nautical procession along the harbor at the festive Lighted Boat Parade.

Read on for more details and more great options—then consult our Event Calendar for our daily selection of activities. Also check out our Summer Fun Guide, with ideas for every aspect of the season!