Your Ultimate Guide to Local Spring Fun
From outdoor festivals to food truck nights and community carnivals, Fairfield County is bursting with events this May. Whether you're looking for something family-friendly, artsy, or foodie-approved, there's something happening near you.
🗓️ May Events Calendar
May 1: Shop & Stroll Into Spring
🕔 5:00 PM – 9:00 PM | 📍 Downtown Fairfield
May 2: Dressed to Impress Gala
🕡 6:30 PM – 11:00 PM | 📍 Penfield Pavilion, Fairfield
May 2–3: Rowayton School Carnival
🕓 May 2: 4:00 PM – 10:00 PM
🕚 May 3: 11:00 AM – 5:00 PM | 📍 1 Roton Ave, Rowayton
May 3–5: Minks to Sinks Tag Sale (Opening Day May 3)
🕘 9:00 AM – 5:00 PM | 📍 395 Danbury Road, Wilton
May 3: Frog Frolic Festival
🕚 11:00 AM – 4:00 PM | 📍 Redding Community Center, Redding
May 4: Mother's Day Pop Shop
🕛 12:00 PM – 5:00 PM | 📍 Elicit Brewing, Fairfield
May 6: Nature Tots – Spring Explorers
🕙 10:00 AM | 📍 CT Audubon Society, Fairfield
May 7–10: Riverfield School Spring Carnival
🕕 6:00 PM – 10:00 PM | 📍 Riverfield Elementary, Fairfield
(Also open May 9 at same time)
May 9: Wilton Mother’s Day Plant Sale
🕘 9:00 AM – 1:00 PM | 📍 Wilton Center Gazebo, Wilton
May 10: Dogwood Festival
🕙 10:00 AM – 5:00 PM | 📍 Greenfield Hill Church, Fairfield
May 11: Mother’s Day Nature Walk
🕙 10:00 AM – 12:00 PM | 📍 New Pond Farm, Redding
May 12: Community Sailing Seminar
🕕 6:00 PM – 8:00 PM | 📍 Fairfield Recreation Center
May 13: Strings – Versatile Vibrations
🕓 4:00 PM – 5:00 PM | 📍 Wilton Library
May 14: Art Exhibit – Martin Kline
🕛 12:00 PM – 5:00 PM | 📍 Heather Gaudio Fine Art, New Canaan
May 15: Elicit Food Truck Night
🕔 5:00 PM – 8:00 PM | 📍 Elicit Brewing, Fairfield
May 16: CT Food Trucks Battle Festival
📍 All Day | Hartford (Hartford County)
May 17: Midcentury Modern Homes Tour
🕐 1:00 PM – 5:00 PM | 📍 Locations across Fairfield & Westport
May 18: Vanessa Trien & The Jumping Monkeys
🕒 3:00 PM | 📍 Edmond Town Hall, Newtown
May 19: Guided Meditation Session
🕕 6:00 PM | 📍 Grounded Meditation, Westport
May 20: Succulent Driftwood Workshop
🕡 6:30 PM | 📍 Elicit Brewing Company, Fairfield
May 21: Community Volunteer Fair
🕚 11:00 AM – 2:00 PM | 📍 Trumbull Library
May 22: Taste of SoNo
🕖 7:00 PM | 📍 The SoNo Collection, Norwalk
May 23:
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Outdoor Movie Night – “The Sandlot” | 🕗 8:00 PM | 📍 Jennings Beach, Fairfield
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Legally Blonde: The Musical | 🕖 7:00 PM | 📍 Fairfield Theatre Company
May 24: On-Field Movie Night
⏰ Time TBD | 📍 Location TBD, Fairfield
May 25: Yo-Yo Ma in Concert
🕖 7:00 PM | 📍 Stamford Center for the Arts, Stamford
May 26: Memorial Day Parades
🕘 Various Times | 📍 Norwalk, Westport, Trumbull
May 27: Make Your Own Sushi Class
🕡 6:30 PM | 📍 Elicit Brewing Company, Fairfield
May 29: Sunset Cruise
🕡 6:30 PM – 8:30 PM | 📍 Norwalk Seaport Association
May 30: FTC Country Dance Party
🕗 8:00 PM | 📍 The Warehouse at FTC, Fairfield
May 31: Ridgefield Spring Stroll
🕙 10:00 AM – 4:00 PM | 📍 Downtown Ridgefield
🧺 Make the Most of May
Be sure to bookmark this post or share it with a friend—there’s something for everyone happening this month. Whether you're a foodie, music lover, family with kids, or just looking to explore more of Fairfield County, May is packed with opportunities to connect and celebrate local life.
Looking for more local guides or real estate tips? Follow along—we’ve got you covered.