Country Fairs, Peach Pie, And Powwows: Here’s What’s Happening In Connecticut This Weekend

CONNECTICUT — Mid-August in Connecticut means open-air markets, small-town fairs, cultural celebrations, and plenty of fresh-picked fruit. From the rolling hills of Litchfield County to the shoreline’s oyster shucking contests, this weekend’s lineup is a sampler platter of the state’s best late-summer traditions. Whether you’re here for the carnival rides, the handmade crafts, or the historic hikes, there’s something for everyone Aug. 15–17.

The 72nd Annual Bridgewater Country Fair, Aug. 15–17, is everything you love about summer in the country—truck pulls, livestock shows, oxen competitions, carnival rides, and the smell of fried dough wafting through the air — squeezed into three days. Hosted by the Bridgewater Volunteer Fire Department, this is one of the region’s most cherished traditions. Friday kicks off with opening ceremonies and live music, while Saturday features a classic parade and fireworks to light up the night sky. Sunday is all about family fun, with contests, farm exhibits, and plenty of old-fashioned charm.

Formerly known as Oysterfest, Saturday's Fair on the Half Shell in downtown Milford is a shoreline summer staple. This year’s rebranded festival keeps the spirit alive with fresh local oysters, food trucks, craft beer, live entertainment, and artisan vendors. It’s a feast for all the senses, set against the backdrop of Milford Harbor. Bring your appetite—and maybe a bib.

Step into centuries of tradition at the Mohegan Wigwam Festival, Saturday and Sunday Mohegan Sun in Uncasville. This celebration of Mohegan culture features traditional dancing, drumming, storytelling, and Native crafts. Visitors can explore Native food booths, watch competitive dances in full regalia, and learn about the Mohegan Tribe’s rich heritage. Admission is free, and the event is open to all.

If you like your festivals sweet, head to Guilford for the Bishop’s Orchards Peach Festival on Saturday. This family-friendly event celebrates peak peach season with pies, cobblers, ice cream, and of course, fresh-picked peaches. There’s live music, kids’ activities, hayrides, and farm animals to meet. Bring a cooler—you’ll want to take some fruit home.

Hike Through History at Gungywamp

On Aug. 16, the Denison Pequotsepos Nature Center leads the Gungywamp Hike in Groton—a guided exploration of ancient stone structures, mysterious chambers, and colonial-era ruins. The site’s layered history stretches from Native American settlements to early European farms, making it a fascinating trek for history buffs and nature lovers alike.

Also on Aug. 16 is the Riverton Grange Fair, a charming agricultural celebration in the northwest hills. Think flower shows, produce contests, homemade baked goods, and small-town hospitality in one of Connecticut’s most scenic hamlets.

On Sunday, Aug. 17, the grand lawns of Middletown’s Wadsworth Mansion host the annual Open Air Market & Festival, a sprawling fair of more than 100 local artisans, farmers, and food vendors. Live music fills the air as visitors browse antiques, art, jewelry, and gourmet treats. Pack a picnic or sample from on-site food trucks while enjoying the estate’s sweeping views.

From the lively parades of Bridgewater to the rhythmic drumbeats of the Mohegan Wigwam Festival, this weekend offers a chance to experience Connecticut’s history, flavors, and community spirit all in one go. Just bring sunscreen, an empty stomach, and maybe a tote bag—you’ll leave with more memories (and way, way more peaches) than you expected.