10 Can't Miss Outdoor Events In Connecticut As Summer Winds Down

CONNECTICUT — Summer is winding down in Connecticut, but there are still some good opportunities to make the most of warm days and long nights before cooler weather sets in and the calendar fills up with fall activities.

The “end-of-the-summer scaries” is a real term for the anxiety and dread that people may feel as the season comes to a close, and they realize they didn’t pack in as much fun as they intended.

As a prescription for end-of-summer malaise, we’ve rounded up 10 things to do outside to enjoy the last bits of summer sunshine.

Are you planning an event this fall? Feature it, so nearby readers see it all across Patch — including in roundups like this.

Here are some upcoming outdoor events you shouldn’t miss:

Running Aug. 21–24, the Brooklyn Fair in Windham County proudly bills itself as the oldest continuously operating agricultural fair in the United States. Founded in 1809, the fair offers everything you’d expect and then some: livestock competitions, midway rides, food courts overflowing with fried treats, live music, and a wide range of exhibits. It’s a perfect mix of old-fashioned charm and modern fairground fun.

Also this weekend, the Black Bear Music Fest (Aug. 22–24) brings three days of jam bands, folk acts, and roots music to the Goshen Fairgrounds. Beyond the tunes, there’s camping, food trucks, and craft vendors for a true festival experience. Families are welcome, and the vibe is more laid-back than rowdy—think hammocks, tie-dye, and fiddles under the stars.

Now in its 12th year, Ridgefield's ArtWalk turns Downtown into a strolling art gallery, beginning Friday, August 22, 5 to 8 p.m., with artist meet and greets outside the stores. Opening weekend continues Saturday, August 23 from noon to 4:00pm with an artists’ day.

The Chester Fair (Aug. 22–24) has been drawing crowds for decades with tractor pulls, animal exhibits, live music, and a famous skillet toss competition. Nestled in the heart of the Connecticut River Valley, this smaller fair packs in plenty of community spirit alongside traditional fair fare.

Another can’t-miss fair runs the same weekend: the Terryville Lions Country Fair, running Aug. 22–24. With truck pulls, livestock barns, arts and crafts, rides, and a demolition derby, this event showcases small-town Connecticut at its best. Proceeds benefit local Lions Club charities, so you’ll be supporting a good cause while you indulge in fried Oreos.

On Saturday, Aug. 23, head to the shoreline for Clinton Summerfest & Fireworks. This daylong celebration includes a street festival, local food vendors, live entertainment, and family activities, all capped off with a fireworks display over Long Island Sound. It’s summer on the shoreline at its finest.

Also on Aug. 23, PorchFest 2025 transforms Old Wethersfield into one big stage as local musicians perform from porches, lawns, and stoops throughout the historic district. Pack a picnic, stroll the streets, and let the music guide you from one performance to the next. It’s one of the state’s most charming music festivals.

Manchester’s Silk City Fest on Aug. 23 celebrates local art, craft beer, and live performances. Expect artisan vendors, street art, food trucks, and a beer garden highlighting regional breweries. Held in the heart of downtown, the event draws thousands each year for a lively mix of creativity and community.

If your perfect weekend includes shopping and snacking, CT Arts & Eats on Aug. 23 delivers with artisan wares, gourmet foods, and live entertainment. Hosted by the Southbury Women’s Club, the event supports local nonprofits while offering a fun day of browsing and bites.

Rounding out the weekend is the 92nd Annual Meetinghouse Rocks Fair in Norwalk on Aug. 23. This beloved community fair combines history, crafts, kids’ games, and plenty of food for a low-key but spirited day out. It’s a reminder that sometimes the best summer memories are made at smaller local fairs.

Whether you’re line-dancing at the Brooklyn Fair, swaying to folk tunes in Goshen, or watching fireworks in Clinton, Connecticut’s late-August weekend is packed with reasons to get outside and celebrate. Just bring your appetite, your dancing shoes, and maybe a lawn chair—you’ll need them all.