Upcoming Events Near Chester

Thursday

Oct 22, 2026

General 1

6:00–8:00 Spy Nights: Conversations with Craig Fuller: Len Foxwell and Clayton Mitchell The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States

Cultural 1

7:30–11:30 Tred Avon Players presents Ravenscroft 200 Oxford Rd, Oxford, MD

Friday

Oct 23, 2026

Cultural 2

7:00–9:00 Cris Jacobs & Pressing Strings A CO-BILL EVENT The Avalon, 40 E Dover Street, Easton, MD, United States
7:30–11:30 Ravenscroft - Tred Avon Players Community Theatre 200 Oxford Rd, Oxford, MD

Saturday

Oct 24, 2026

Family 1

12:00 Special Italian Experience and In-Shop Wine Tasting with Sisto Tessari! 104 Railroad Ave, Saint Michaels, MD, United States, Maryland 21663, 104 Railroad Ave, St Michaels, MD 21663-2125, United States

1

Cultural 3

9:00–12:30 Colonel Tench Tilghman Week Easton, MD, 100 W Dover St, Easton, MD 21601, USA
7:00–9:00 Amy Speace with special guest Jesse Lynn Madera The Avalon, 40 E Dover Street, Easton, MD, United States
7:30–11:30 Ravenscroft - Tred Avon Players Community Theatre 200 Oxford Rd, Oxford, MD

Sunday

Oct 25, 2026

Cultural 1

7:30–10:00 Neko Case The Avalon, 40 E Dover Street, Easton, MD, United States

Monday

Oct 26, 2026

1

Tuesday

Oct 27, 2026

Cultural 1

9:00–12:00 Poplar Island Tours Poplar Island, 21548 Chicken Point Rd, Tilghman, MD 21671, USA

Wednesday

Oct 28, 2026

Family 1

3:00–3:00 OCC Classic Cinema Club – Shadow of a Doubt Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA

Thursday

Oct 29, 2026

Cultural 3

5:30–6:45 Freedom Ship: The Uncharted History of Escaping Slavery by Sea 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States
7:00–9:00 Stillhouse Junkies The Avalon, 40 E Dover Street, Easton, MD, United States
7:30–6:00 Ravenscroft 200 Oxford Rd, Oxford, MD

Friday

Oct 30, 2026

Cultural 1

7:30–6:00 Ravenscroft 200 Oxford Rd, Oxford, MD

Saturday

Oct 31, 2026

Family 1

TBD Halloween Festival 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States

Cultural 2

8:00–4:00 Historic Drawbridge Running Festival Burns St, St Michaels, MD
7:30–6:00 Ravenscroft 200 Oxford Rd, Oxford, MD

Sunday

Nov 1, 2026

Cultural 1

7:30–6:00 Ravenscroft 200 Oxford Rd, Oxford, MD

Thursday

Nov 5, 2026

Family 1

5:00–7:00 Family Law Clinic Centreville Conference Room

Cultural 1

7:00–9:00 Jake Shimabukuro The Avalon, 40 E Dover Street, Easton, MD, United States

Saturday

Nov 7, 2026

Family 1

10:00–4:00 CBMM's OysterFest Chesapeake Bay Maritime Museum, 38.787516, -76.220082

Cultural 1

10:00–8:00 6th Annual Shore Good Truck Show and Pull 11472 Ocean Gateway, Easton, MD 21601

Thursday

Nov 12, 2026

Cultural 3

7:00–9:00 Ali Webb & Friends The Avalon, 40 E Dover Street, Easton, MD, United States
12:00–12:00 Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD
TBD Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD

Friday

Nov 13, 2026

Cultural 3

7:00–9:00 Chloe Kimes: Daredevil Tour The Avalon, 40 E Dover Street, Easton, MD, United States
12:00–12:00 Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD
TBD Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD

Saturday

Nov 14, 2026

Cultural 3

7:30–9:00 Next Generation Showcase ‘26 17 South Washington Street, Easton, MD, USA
12:00–12:00 Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD
TBD Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD

Sunday

Nov 15, 2026

General 1

1:00–1:00 The Lost Trees of Willow Ave with Mike Tidwell Cadby Theatre, 1000 College Cir, Wye Mills, MD 21679, USA

Cultural 2

12:00–12:00 Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD
TBD Waterfowl Festival Premier Night Tickets 101 E Dover St, Easton, MD

Wednesday

Nov 18, 2026

Cultural 1

7:30–9:30 VIVA VERDI | Ludovic Tézier | Midweek Gala Night 17 South Washington Street, Easton, MD, USA

Upcoming events near Chester