Pirates, Parades, And Produce: Connecticut’s Weekend Events Pack Plenty Of Fun

CONNECTICUT — From seafaring scallywags to blueberry bliss, Connecticut is bursting with summer fun this weekend. Whether you're itching to don your eye patch, browse artisan crafts, or simply savor something sweet, there’s something for everyone happening July 18–20 across the Nutmeg State.

We're not exactly sure why, and are probably better off not knowing, but pirate-themed fun is taking over Connecticut this weekend with not one, but two high-seas style events.

Kick things off in Norwalk with the return of the Sheffield Island Pirates Weekend Ferry, Saturday and Sunday, July 19–20. This family-friendly voyage sets sail from the new dock located at 70 Water Street in South Norwalk and whisks passengers to the historic Sheffield Island Lighthouse for pirate-themed games, storytelling, and treasure hunts. The ferry departs the dock at 11:00 a.m., 12:30 p.m. and 2:00 p.m. on both days. Tickets and details are available here and here.

If you’d rather ride the rails than the waves, head to Essex for the Pirate Family Adventures aboard the Essex Steam Train on Saturday, July 19. Little buccaneers can meet pirate characters, join a hunt for stolen treasure, and learn a thing or two about life on the high seas. Book your boarding pass here.

Ancient Drums, Modern Thrills

History and music lovers alike will want to mark their calendars for the Deep River Ancient Muster & Parade, also on Saturday. This long-running tradition celebrates fife and drum corps with performances from across the region. Expect colorful colonial garb, rousing music, and a whole lot of patriotic pride. Plan your visit here.

Shopping, Snacks, and Small-Town Charm

On Friday and Saturday. July 18–19, downtown New Canaan transforms into a vibrant open-air marketplace with the 2025 New Canaan Village Fair and Sidewalk Sale. Local merchants spill out onto the sidewalks and will be joined by close to 100 other vendors and organizations from all over Fairfield County with deals, giveaways, and games. Local nonprofits and entertainers add to the festive atmosphere. Full details can be found here.

Meanwhile, over in Middlefield, fruit lovers can flock to the Blueberry Festival at Lyman Orchards on Saturday, July 19. Celebrate peak blueberry season with farm-fresh treats, live music, food trucks, pie-eating contests and yoga classes. Gates open at 8 a.m., full schedule of events is here.

Art in the Hills

Artisans and handmade craft lovers, don’t miss the 5th Annual Litchfield County Artisans Festival on Saturday. Set against the scenic backdrop of the New Milford Town Green, this juried show features jewelry, textiles, pottery, woodworking, and more. Details for the event are available here.

Dino Days Roll On

And if you're traveling with a future paleontologist, don't forget that DINO-Trolley continues through Sunday, July 20, at the Connecticut Trolley Museum in East Windsor. Young explorers can ride a historic trolley, dig for fossils, and meet life-sized dinosaur puppets. Get your prehistoric tickets here.

With events ranging from pirates to pancakes and crafts to Cretaceous creatures, there’s no shortage of ways to enjoy this July weekend in Connecticut. Wherever your summer takes you, don’t forget your sunscreen—and maybe a tricorn hat.