Labor Day weekend marks the unofficial end of summer—and Fairfield County families have plenty of ways to celebrate. From county fairs to food festivals, jazz music to pet parades, there’s no shortage of events happening within driving distance. Whether you’re looking for a classic New England fairground experience or something totally unique (like knights and jesters at the Renaissance Faire), here are 8 destinations you’ll want to check out this long weekend.
-
St. Leo Fair – Stamford, CT – Through Sat Aug 30
A Fairfield County favorite, St. Leo’s offers classic carnival rides, food stands, and bingo nights. Perfect for families who want fun close to home. -
Woodstock Fair – Woodstock, CT – Aug 28-Sep 1
Known as one of Connecticut’s biggest fairs, Woodstock has it all: farm animals, craft contests, food vendors, and that nostalgic fairground magic. -
Haddam Neck Fair – Haddam, CT – Aug 29-Sep 1
This annual tradition features a petting zoo, rides, and live entertainment throughout the day—ideal for kids of all ages. -
Bridgeport Jazz Festival – Bridgeport, CT – Sat Aug 30
For music lovers, McLevy Green transforms into an open-air jazz venue with incredible performances and good vibes. -
Fairfield International Food Festival – Fairfield, CT – Sat Aug 30
Take your taste buds on a trip around the world with street food, art vendors, and live performances across multiple stages. -
Connecticut Renaissance Faire – Lebanon, CT – Saturdays & Sundays – Aug 30-Oct 19, 2025 – plus Labor Day and Columbus Day Mondays
Step back in time with knights, jesters, jousts, and artisan vendors. A unique family outing that mixes history, fun, and fantasy. -
Goshen Fair – Goshen, CT – Aug 30-Sep 1
This classic fair offers lumberjack contests, livestock shows, pie-eating competitions, and even fireworks. A true slice of small-town Americana. -
Newtown Labor Day Pets on Parade – Newtown, CT – Sep 1
Celebrate hometown pride with a whimsical parade featuring pets, floats, and community spirit.
Whether you’re in the mood for rides, music, food, or fireworks, Fairfield County and its neighbors have something for everyone this Labor Day weekend. With events spread across Connecticut, you can pick one or try to fit in a few before summer says goodbye.
✨ End summer on a high note – where are you headed first?
Contact me here:
📞 Joe Balestriere, Realtor®
📲 Call/Text: 203-216-0670
