14 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.
What's coming up
Westport Farmers Market Thu 6 Aug 2026, 10:00 AM — Market Imperial Avenue lot · 50 Imperial Ave, Westport, CT 06880 · Free entry
Comedy Night! Tue 15 Sep 2026, 6:00 PM — Comedy Levitt Pavilion for the Performing Arts · 40 Jesup Rd, Westport, CT 06880 · Free (free-ticket show; reserve online or at the box office 2 hours before showtime)
Westport Community Band Wed 16 Sep 2026, 6:00 PM — Live music Levitt Pavilion for the Performing Arts · 40 Jesup Rd, Westport, CT 06880 · Free (free-ticket show; reserve online or at the box office 2 hours before showtime)
King Stingray Wed 23 Sep 2026, 6:30 PM — Live music Levitt Pavilion for the Performing Arts · 40 Jesup Rd, Westport, CT 06880 · Free (free-ticket show; reserve online or at the box office 2 hours before showtime)
Speed Dating Ages 30-45 in Westport, CT at The Clubhouse Westport Wed 23 Sep 2026, 7:00 PM — social The Clubhouse Westport · 1620 Post Road East, Westport, CT 06880
Ailey II: The Next Generation of Dance Thu 24 Sep 2026, 7:00 PM — Theater Westport Country Playhouse · 25 Powers Ct, Westport, CT 06880 · $80/$80/$75
Harvest Fest 2026 Sat 26 Sep 2026, 6:00 PM — Festival Wakeman Town Farm · 134 Cross Highway, Westport, CT 06880
Script In Hand: TBA (October playreading) Mon 5 Oct 2026, 7:00 PM — Theater Westport Country Playhouse · 25 Powers Ct, Westport, CT 06880 · $35 ($30 series subscribers/Encore Club)
Nutmeg Listening Room Featuring Drew Ryder Smith & Melissa Capezio Fri 9 Oct 2026, 7:00 PM — Live music Veterans of Foreign Wars · 465 Riverside Avenue, Westport, CT 06880
Gay Speed Dating Ages 21+ in Westport, CT at The Clubhouse Westport Thu 15 Oct 2026, 7:00 PM — social The Clubhouse Westport · 1620 Post Road East, Westport, CT 06880
October Comedy Blowout @ The VFW Westport Fri 16 Oct 2026, 8:00 PM — Comedy Veterans of Foreign Wars · 465 Riverside Avenue, Westport, CT 06880
Beer Garden - An Outdoor Fall Event for the entire family Sun 18 Oct 2026, 12:00 PM — Live music Wakeman Town Farm · 134 Cross Highway, Westport, CT 06880
Halloween Night Speed Dating in Westport, CT at The Clubhouse Westport Thu 29 Oct 2026, 7:00 PM — social The Clubhouse Westport · 1620 Post Road East, Westport, CT 06880
Spadtastics Encore Sat 14 Nov 2026, 7:00 PM — Live music Trefz Forum @ the Westport Library - Downtown Westport · 20 Jesup Road, Westport, CT 06880
Listings are seeded from venue and organiser calendars. See them on the map.