Things to do this weekend in and around Fairfield County
Friendly fun in Fairfield County for Friday, September 5, 2026 through Sunday, September 7, 2026. Check out these highlights!
(Scroll down for full list of weekend activities.)
Friday, September 5, 2026
FREE fall and holiday mini photo sessions with Shoott! - Connecticut - September 5-7, 2026 - New York, NY. Enjoy a free 30-minute outdoor photo session and receive a gallery of professionally edited images to choose from for your holiday cards and family memories.
Tedeschi Trucks Band w/Sheryl Crow, Saturday, September 5, 7:00PM - September 5, 2026 - Bridgeport, CT. Catch a powerhouse night of live music as Tedeschi Trucks Band and Sheryl Crow take the stage at Hartford HealthCare Amphitheater.
Fairfield International Food Fest - September 5, 2026 - Fairfield, CT. Sample a delicious variety of international cuisines and enjoy a festive atmosphere at Fairfield Theatre Company.
Little Red Bar[n] Live Music at Bishop's Orchards - September 5, 2026 - Guilford, CT. Relax with an evening of live music at the Little Red Barn while you savor local food and drinks at Bishop's Orchards.
Family Field Day at Mystic Seaport Museum - September 5, 2026 - Mystic, CT. Spend the day exploring outdoor activities and family-friendly fun across the historic grounds of Mystic Seaport Museum.
Saturday, September 6, 2026
Corn Maze & Cider Donut Festival - September 5-6, 2026 - Middlefield, CT. Navigate a fun corn maze and indulge in fresh cider donuts and seasonal treats at Lyman Orchards.
Goshen Fair 2026 - September 5-7, 2026 - Goshen, CT. Enjoy a classic country fair with agricultural exhibits, family entertainment, rides, and fair food all weekend long.
35th Annual JPMorgan Chase Hudson Valley Hot Air Balloon Festival - September 5-6, 2026 - Poughkeepsie, NY. Watch colorful hot air balloons lift off, explore family activities, and enjoy food and entertainment along the Hudson River.
Fall Festival at Outhouse Orchards - September 5-7, 2026 - North Salem, NY. Celebrate the start of fall with apple picking, hayrides, and seasonal farm fun at Outhouse Orchards.
Bluegrass, Beer & BBQ at Harvest Moon Farm and Orchards - September 5-6, 2026 - North Salem, NY. Enjoy live bluegrass music paired with craft beverages and barbecue in a scenic orchard setting.
Sunday, September 7, 2026
The 28th Annual Connecticut Renaissance Faire - September 5-7, 2026 - Lebanon, CT. Step into a medieval village with costumed performers, jousting, marketplace vendors, and family-friendly shows.
Shore Line Trolley Museum America 250 Wayback Fare Day – Ride at 2016 Prices - September 5, 2026 - East Haven, CT. Ride historic trolleys along the scenic shoreline while enjoying special throwback fares to celebrate America 250.
Connecticut River Museum Special Exhibit: Rhythm of the River: Music and Memory Along the Connecticut - September 5-6, 2026 - Essex, CT. Explore a special exhibit highlighting the musical heritage and stories connected to the Connecticut River.
Movie Event - Smurfs (2025) - September 5, 2026 - Stamford, CT. Bring the kids to a fun screening of the Smurfs (2025) movie at Stamford Town Center.
OPEN FARM DAY at Common Ground High School, Urban Farm, and Environmental Education Center - September 5, 2026 - New Haven, CT. Visit the urban farm to meet the animals, explore gardens, and learn about sustainable agriculture and environmental education.