Fairs, Food, and Festivals: Here’s What’s Happening Across Connecticut This Labor Day Weekend

CONNECTICUT — Labor Day weekend — the unofficial "end of summer" — is here, and Connecticut is going out with a bang. From classic country fairs to Greek dancing, cider donuts, and global eats, this holiday stretch offers one last hurrah before summer slips into September. Whether you’re looking for livestock shows, carnival rides, or a chance to explore a corn maze with donut in hand, the Nutmeg State has you covered Aug. 29–Sept. 1.

Few things say summer in Connecticut like the Haddam Neck Fair, running Aug. 29–Sept. 1. Hosted by the Haddam Neck Agricultural Society, this classic country fair is known for its tractor pulls, demolition derby, midway rides, and plenty of live entertainment. Livestock exhibits and agricultural displays highlight the region’s farming roots, while food vendors serve up fried dough, sausages, and all the fair classics. Families won’t want to miss the fireworks and nightly concerts.

Not to be outdone, and also running through Labor Day weekend, is the legendary Woodstock Fair, one of the largest agricultural fairs in New England. The sprawling fairgrounds feature horse shows, craft barns, produce contests, and a jam-packed schedule of concerts. This year’s entertainment lineup ranges from country bands to tribute acts, and the midway is filled with rides and games to keep kids busy for hours.

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In the Litchfield Hills, the Goshen Fair, from Aug. 30–Sept. 1, is another Labor Day staple. A mix of rural tradition and family fun, the fair features oxen pulls, horse shows, tractor contests, and an impressive lineup of vendors selling everything from farm goods to handmade crafts. Live music and food stands keep the energy high, making it a must for anyone looking to savor a true New England ag fair experience.

If you’d rather spend your weekend with gyros and baklava, head to Orange for Odyssey ’25: A Greek Festival, held at St. Barbara Greek Orthodox Church from Aug. 29–Sept. 1. This Labor Day tradition offers authentic Greek cuisine, traditional dancing, live music, and cultural exhibits. Don’t leave without sampling the loukoumades (honey puffs) and spanakopita.

For a taste of the world closer to home, we have high hopes for the Fairfield International Food Fest debuting on Aug. 30 with global cuisines, craft vendors, and live entertainment. From Asian street food to Latin flavors, the event promises to be a culinary passport without leaving the state.

Nothing ushers in autumn like apples and donuts, and the Corn Maze & Cider Donut Festival (Aug. 30–31) at Lyman Orchards in Middlefield bridges the seasons perfectly. Guests can explore the farm’s famous corn maze, enjoy fresh cider donuts, and stock up on produce at the farm store. Live music and kids’ activities make this a family-friendly favorite.

If your idea of a perfect weekend involves live music and cold beer, the Lonely Roads Fest in Stafford (Aug. 30) delivers. This outdoor festival combines local breweries with a strong lineup of regional bands for a day of great tunes and tasty pours.

From corn mazes to carnival rides, Greek folk dancing to fireworks, Connecticut is closing out summer in style. Pack your appetite, wear comfortable shoes, and make room on your camera roll or smartphone—you’ll want to capture every moment of this long weekend.