Old Saybrook Events 2026-2027
Your guide to live events and things to do in Old Saybrook, CT, and nearby areas.
- Updated: October 30, 2026
Events take place across Old Saybrook throughout 2026, including major concerts, sports, and live performances happening every week. Browse by date, venue, or category to find what’s happening near you.
- 39 Upcoming Events
- 4 Events This Weekend
- 1 Event Venue
- 8 Event Categories
Browse Events By Category
- All Events 39
- concerts 25
- broadway 2
- Live Shows 13
- comedy 1
- This Weekend 4
Best Events This Week & This Month
Explore featured Old Saybrook events including top shows, concerts, sports, and major live experiences across the city.
Old Saybrook Events: Today, This Month & Dates
Upcoming Events in Old Saybrook
Browse events in 2026 by date and venue, including concerts, shows, sports, and more across the city and nearby areas.Upcoming Confirmed Events 39
- Oct 31, 2026, 2:30 PM Sat — MUSICAL / PLAY, Weekend Event: Sister's Back to School Catechism at The Katharine Hepburn Cultural Arts Center,
300 Main St, Old Saybrook, CT 06475, US. From $66, Avg. price ~ $145, Tickets Available: 123. Select Seats - Oct 31, 2026, 7:30 PM Sat — MUSICAL / PLAY, Weekend Event: Sister's Back to School Catechism at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $71, Avg. price ~ $139, Tickets Available: 121. Select Seats
- Nov 01, 2026, 1:00 PM Sun — 50s / 60s ERA, Weekend Event: Vintage Vixens at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $59, Avg. price ~ $147, Tickets Available: 111. Select Seats
- Nov 01, 2026, 7:30 PM Sun — R&B / SOUL, Best Value, Weekend Event: Zambonis & Big Fat Combo at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $35, Avg. price ~ $47, Tickets Available: 95. Select Seats
- Nov 04, 2026, 7:30 PM Wed — POP / ROCK: The Fabulous Thunderbirds at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $273, Avg. price ~ $371, 23 tickets remaining! Select Seats
- Nov 05, 2026, 7:30 PM Thu — POP / ROCK: Jimmy Webb at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $80, Avg. price ~ $324, 25 tickets remaining! Select Seats
- Nov 06, 2026, 8:00 PM Fri — COUNTRY / FOLK: John Sebastian & Jimmy Vivino at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $99, Avg. price ~ $114, 2 tickets remaining! Select Seats
- Nov 07, 2026, 8:00 PM Sat — POP / ROCK, Weekend Event: John Cafferty and The Beaver Brown Band at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $273, Avg. price ~ $371, 23 tickets remaining! Select Seats
- Nov 08, 2026, 7:00 PM Sun — Concert, Weekend Event: Total Mass Retain - YES Tribute Band at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $51, Avg. price ~ $115, Tickets Available: 121. Select Seats
- Nov 10, 2026, 7:30 PM Tue — POP / ROCK: Jesse Cook at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $94, Avg. price ~ $327, 25 tickets remaining! Select Seats
- Nov 13, 2026, 8:00 PM Fri — POP / ROCK: Frontiers at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $61, Avg. price ~ $182, Tickets Available: 52. Select Seats
- Nov 14, 2026, 2:00 PM Sat — Concert, Weekend Event: Yellow Brick Road at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $273, Avg. price ~ $371, 23 tickets remaining! Select Seats
- Nov 15, 2026, 2:00 PM Sun — JAZZ / BLUES, Weekend Event: Bela Fleck at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $273, Avg. price ~ $371, 23 tickets remaining! Select Seats
- Nov 15, 2026, 7:00 PM Sun — JAZZ / BLUES, Weekend Event: Bela Fleck at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $273, Avg. price ~ $371, 23 tickets remaining! Select Seats
- Nov 16, 2026, 7:30 PM Mon — POP / ROCK, High Demand: John Splithoff at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $967, Avg. price ~ $1,116, 4 tickets remaining! Select Seats
- Nov 17, 2026, 7:30 PM Tue — POP / ROCK, High Demand: Marshall Crenshaw at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $66, Avg. price ~ $189, Tickets Available: 102. Select Seats
- Nov 19, 2026, 7:30 PM Thu — Concert: Hollywood Nights - Bob Seger Tribute at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $80, Avg. price ~ $92, 2 tickets remaining! Select Seats
- Nov 20, 2026, 8:00 PM Fri — Concert: Hollywood Nights - Bob Seger Tribute at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $273, Avg. price ~ $371, 23 tickets remaining! Select Seats
- Nov 21, 2026, 8:00 PM Sat — Concert, Weekend Event: Return to Paradise - Tribute to Styx at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $65, Avg. price ~ $105, Tickets Available: 32. Select Seats
- Nov 22, 2026, 7:00 PM Sun — ALTERNATIVE, Weekend Event: Griffin House at The Katharine Hepburn Cultural Arts Center, 300 Main St, Old Saybrook, CT 06475, US. From $46, Avg. price ~ $65, Tickets Available: 113. Select Seats
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Old Saybrook Events by Month
Monthly pages help you find upcoming events by season, weekend, and date.
Events by Show & Venue
Browse Old Saybrook events by show and venue. Explore performance schedules, event counts, and upcoming dates across the city.
Sister's Back to School Catechism
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 2
Oct 31, 2026 2:30 PM
Vintage Vixens
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 1
Nov 01, 2026 1:00 PM
Zambonis
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 1
Nov 01, 2026 7:30 PM
The Fabulous Thunderbirds
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 5
Nov 04, 2026 7:30 PM
Jimmy Webb
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 6
Nov 05, 2026 7:30 PM
John Sebastian
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 1
Nov 06, 2026 8:00 PM
John Cafferty and The Beaver Brown Band
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 5
Nov 07, 2026 8:00 PM
Total Mass Retain - YES Tribute Band
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 2
Nov 08, 2026 7:00 PM
Jesse Cook
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 34
Nov 10, 2026 7:30 PM
Frontiers
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 1
Nov 13, 2026 8:00 PM
Yellow Brick Road
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 3
Nov 14, 2026 2:00 PM
Bela Fleck
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 15
Nov 15, 2026 2:00 PM
John Splithoff
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 35
Nov 16, 2026 7:30 PM
Marshall Crenshaw
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 8
Nov 17, 2026 7:30 PM
Hollywood Nights - Bob Seger Tribute
300 Main St, Old Saybrook, CT 06475
Upcoming Events: 11
Nov 19, 2026 7:30 PM
From long-running shows to packed venues, this list breaks down what’s playing across Old Saybrook. Check schedules, event counts, and upcoming dates by show and location.
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Frequently Asked Questions
Quick answers about tickets, prices, and game day details.
What events are happening in Old Saybrook right now?
A little bit of everything — concerts, shows, sports, comedy. Old Saybrook rarely sits still. Check the schedule above to see what’s happening today, this week, or whenever you finally make plans.
How often is the event schedule updated?
Pretty often — like, more than your group chat actually commits to plans. New events get added as soon as dates and venues are confirmed.
Can I browse events by date or venue?
Yep. Filter by date, venue, or category and skip the endless scrolling. Your future self will appreciate it.
Are events held year-round in Old Saybrook?
Yeah — Old Saybrook doesn’t really take a season off. There’s always something going on, even when the weather’s doing its thing.
Where do events take place in Old Saybrook?
Everywhere — arenas, theaters, stadiums, clubs, and venues across Old Saybrook, CT. Big stages, small stages, and everything in between.
Do new events get added regularly?
All the time. If a tour drops or a game gets scheduled, it usually shows up here faster than you hear about it from friends.
Browse Events by Category
Find concerts, sports, theatre, comedy, and more in Old Saybrook and nearby areas
Events Near Old Saybrook
Here's what's happening nearby.
About American Arenas®
American Arenas® is a live-events platform that connects event schedules, venues, and ticket options through trusted marketplace partners. Listings are updated regularly as new events and dates are confirmed, helping users discover what’s happening and explore available ticket options across concerts, sports, shows, and more.