Upcoming Events Near Chester

Today

Sep 20, 2026

Family 1

3:00–7:00 Community Harvest Supper 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States

Cultural 1

2:00 Alice by Heart presented by Church Hill Theatre Church Hill Theatre

Tomorrow

Sep 21, 2026

General 1

10:00–2:00 Operation Paws for Homes Animal Adoption The Mill of Kingstown Address: 7121 Church Hill Rd, Chestertown, MD 21620 Join us at The Mill of Kingstown on Monday, September 21 from 10:00am to 2:00pm for an animal adoption event hosted by Operati

Tuesday

Sep 22, 2026

1

Cultural 1

5:45–6:45 Yoga on Navy Point 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States

Wednesday

Sep 23, 2026

Cultural 1

5:00–8:00 Live music at Foxy’s! Groove Tide! 🌊🌴🎶☀️ 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States

Thursday

Sep 24, 2026

General 1

10:00–2:00 Livestock Q&A with Kendall Clark The Mill of Kingstown Address: 7121 Church Hill Rd, Chestertown, MD 21620 Join us at The Mill of Kingstown on Thursday, September 24 from 10:00am to 2:00pm for a Livestock Q&A with Kendall Clark. Even

Cultural 2

5:30–7:30 Summer Nature Journaling: Migration and Climate Change in the Wetlands Pickering Creek Audubon Center, 11450 Audubon Ln, Easton, MD 21601, USA
7:00–9:00 The Wailers The Avalon, 40 E Dover Street, Easton, MD, United States

Friday

Sep 25, 2026

General 2

6:00–10:00 Crabbing the Miles River 213 N Talbot St, St Michaels, MD
8:00–10:00 Transformers One - Outdoor Movie Night @ Idlewild Park (Sponsored by Preston Automotive) 115 Idlewild Ave, Easton, MD 21601-2814, United States, 115 Idlewild Ave, Easton, MD 21601-2814, United States

Sports 2

7:00 Magic the Gathering: Reality Fracture Prerelease Kent Island
7:00 Magic the Gathering: Reality Fracture Prerelease Easton

Family 1

11:00–1:00 Early Education Day at CBMM 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States

1

Cultural 9

6:00–10:00 Crabbing the Miles River 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States
4:45–6:30 A Toast to White House History 17 South Washington Street, Easton, MD, USA
5:30–7:00 Aerospace Talk with Terry J. Hart - 1984 Space Shuttle Challenger Astronaut Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
6:00–9:00 Live music at Foxy’s! Dave Hawkins! 🎶🎶 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States
7:00–9:00 Brett Dennen - Art is Life Tour The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States
7:00–9:00 Brett Dennen - Art is Life Tour The Avalon, 40 E Dover Street, Easton, MD, United States
7:00–9:00 Brett Dennen: Art is Life Tour The Avalon, 40 E Dover Street, Easton, MD, United States
7:00–9:00 Julian Velard The Avalon, 40 E Dover Street, Easton, MD, United States
7:30 Alice by Heart presented by Church Hill Theatre Church Hill Theatre

Saturday

Sep 26, 2026

General 2

11:00–5:00 Ricks Rollin Restaurant Food Truck The Mill of Kingstown Address: 7121 Church Hill Rd, Chestertown, MD 21620 Join us at The Mill of Kingstown on Saturday, September 26 as Ricks Rollin Restaurant pulls up from 11:00am to 5:00pm. Event D
7:00–9:00 2026 Bailando con las Estrellas (Dancing with the Stars) 40 E Dover St, Easton, MD

Sports 5

12:00 Lorcana Attack of the Vine Set Championship Kent Island
12:00 Pokémon League Cup Easton
12:00 Riftbound Vendetta Summoner Skirmish II Kent Island
3:00 Star Wars Unlimited Ashes of the Empire Store Showdown Easton
6:00 Gundam Card Game ST11-14 Release Event Easton

Family 1

7:00–2:00 Dreamers Reprise Dance Performance Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA

1

Cultural 12

10:00–4:30 Frederick Douglass Day 2026 11 N Washington St, Easton, MD 21601-3195, United States, 11 N Washington St, Easton, MD 21601-3195, United States
12:00–3:30 The Abruzzo Italian Table: A Regional Food & Wine Experience - 2 Times: 12 Noon or 2:00 PM Simpatico Italy's Finest Saint Michaels, 104 Railroad Ave, St Michaels, MD 21663, USA
12:00–3:30 The Abruzzo Italian Table: A Regional Food & Wine Experience - 2 Times: 12 Noon or 2:00 PM Simpatico Saint Michaels, 104 Railroad Ave, St Michaels, MD 21663, USA
5:00–8:00 Live music at Foxy’s! Dragon cats! 🐈‍⬛ 🎶🐉 125 Mulberry St, Saint Michaels, MD, 125 Mulberry St, St Michaels, MD 21663, United States
7:00 Bailando con las Estrellas Avalon Theatre, 40 E Dover St, Easton, MD 21601, USA
7:00–9:00 Chesapeake Multicultural Center's Bailando con las Estrellas 40 East Dover Street, Easton, MD, USA
7:00–9:00 Julian Velard Avalon Foundation Inc, The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States
7:00–10:30 Julian Velard Avalon Foundation Inc, 40 E Dover St, Easton, MD
7:30–10:30 2026 Bailando con las Estrellas (Dancing with the Stars) 40 E Dover St, Easton, MD
7:30–7:30 Chesapeake Music presents ArcoStrum with Violinist Strauss Shi and Guitarist TY Zhang 17 South Washington Street, Easton, MD, USA
7:00–3:00 Continuum Dance Performance: Dreamers Reprise 200 Oxford Road, Oxford, MD 21654
7:30 Alice by Heart presented by Church Hill Theatre Church Hill Theatre

Sunday

Sep 27, 2026

Sports 1

11:30 Age of Sigmar Spearhead Tournament Easton

Family 1

7:00–2:00 Dreamers Reprise Dance Performance Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA

Cultural 2

7:00–3:00 Continuum Dance Performance: Dreamers Reprise 200 Oxford Road, Oxford, MD 21654
2:00 Alice by Heart presented by Church Hill Theatre Church Hill Theatre

Monday

Sep 28, 2026

Sports 1

6:00 Lorcana Booster Draft Tournament Kent Island

Cultural 2

10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States

Tuesday

Sep 29, 2026

General 1

6:00–6:00 Outdoor Movie Nights Inn at Perry Cabin, 308 Watkins Ln, St Michaels, MD 21663, USA

Sports 1

6:00 Lorcana Booster Draft Tournament Easton

Cultural 4

5:45–6:45 Yoga on Navy Point 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States
8:00–10:00 Summer Cinema on Linden Lawn 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States

Wednesday

Sep 30, 2026

General 1

10:00–1:00 Nobel Garden Tour Londonderry on the Tred Avon, Easton, MD, USA

1

Cultural 3

3:00–6:00 OCC Classic Cinema Club and the Oxford Museum Presents ‘1776’ Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States

Thursday

Oct 1, 2026

General 1

8:00–1:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD

Sports 1

6:00 Gundam Card Game ST11-14 Release Event Kent Island

Family 1

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

Cultural 2

10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States

Friday

Oct 2, 2026

General 1

5:00–9:00 Easton's Fall Kickoff 11 S Harrison St, Easton, MD, United States, Maryland 21601, 11 S Harrison St, Easton, MD 21601-3042, United States

Cultural 9

5:00–9:00 Easton's Fall Kickoff
5:00 First Friday Gallery Walk 11 S Harrison St, Easton, MD, United States, Maryland 21601, 11 S Harrison St, Easton, MD 21601-3042, United States
5:00–7:00 First Friday Gallery Walk North Harrison Street, Easton, MD, USA
8:30 Hotel Transylvania - Outdoor Movie Night @ The Academy Art Museum (Sponsored by Framptom) 106 South Street, 106 South St, Easton, MD 21601-2917, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States
12:00–12:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
10:00–3:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD
TBD Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD

Saturday

Oct 3, 2026

Family 1

7:00–9:00 Kat Parsons - The Sweetness Is Now: A Release Concert The Avalon, 40 E Dover Street, Easton, MD, United States

1

Cultural 11

12:00–2:00 Bookmaking Workshop & Presentation on Saturday, October 3rd, 2026 from 12-2pm at 9s Studios & Gallery 9 S Harrison St unit 9a, Easton, MD, USA
1:00–4:00 The Met: Live in HD Così fan tutte by Wolfgang Amadeus Mozart The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States
2:30 Haunted Tales of St. Michaels 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States
6:00–6:00 A night in Madrid - Fall Fundraiser Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
6:00 Gundam Card Game 1st Anniversary Event Easton
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States
12:00–12:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
10:00–3:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD
TBD Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
12:00–12:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD

Sunday

Oct 4, 2026

Cultural 7

3:00–4:00 Concert – The Chivalrous Crickets The Church of the Holy Trinity, 502 S Morris St, Oxford, MD 21654, USA
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States
12:00–12:00 Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
10:00–3:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD
TBD Intro to Sailing Small Craft 213 N Talbot St, St Michaels, MD
12:00–12:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD

Monday

Oct 5, 2026

Cultural 3

10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States
12:00–12:00 Mid-Atlantic Small Craft Festival 213 N Talbot St, St Michaels, MD

Tuesday

Oct 6, 2026

Cultural 4

5:30–6:45 The Smithsonian Environmental Research Center: Ecosystem Science for the Chesapeake Bay's Future 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States
5:45–6:45 Yoga on Navy Point 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 101 N Harbor Rd, St Michaels, MD 21663-2910, United States
10:00–1:00 ASA 114 - Cruising Catamaran Certification: Aboard Epiphany 101 N Harbor Road, Saint Michaels, MD, United States, Maryland 21663, 310 N Harbor Rd, St Michaels, MD 21663, United States

Thursday

Oct 8, 2026

General 1

4:30–8:00 Wild Bird Dinner at The Elks Lodge Elks Lodge Address: 8631 Bell Rose Ln Chestertown, MD 21620-4501 Join us at the Elks Lodge on Thursday, October 8 for A Night for the Birds, The Mill's Wild Bird Dinner and Program on the Eastern Shor

Family 2

5:00–5:00 Chesapeake Film Festival Easton, MD, USA
6:00–8:00 Hispanic Heritage Month Poster Contest - Winners Announcement Reception Academy Art Museum, 106 South St, Easton, MD 21601, USA

Cultural 3

4:00–8:00 2nd Annual Circle of Hope Breast Cancer Awareness and Community Celebration Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA
7:00–9:00 An Evening with The Del McCoury Band The Avalon, 40 E Dover Street, Easton, MD, United States
TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA

Friday

Oct 9, 2026

General 1

5:30–5:30 From Memoir to Movement with Dana Soon Burgess Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA

Cultural 2

7:00–9:00 Lee Fields The Avalon, 40 E Dover Street, Easton, MD, United States
TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA

Saturday

Oct 10, 2026

General 1

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

Sports 1

12:00 Pokémon League Cup Kent Island

Cultural 1

TBD 19th Annual Chesapeake Film Festival Oct 8-10 17 South Washington Street, Easton, MD, USA

Sunday

Oct 11, 2026

Cultural 1

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

Wednesday

Oct 14, 2026

Family 1

5:30 Financial Wellness Estate Planning Basics Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA

Cultural 1

7:00–9:00 Oh He Dead The Avalon, 40 E Dover Street, Easton, MD, United States

Thursday

Oct 15, 2026

Family 1

5:00–7:00 Family Law Clinic Kent Island 118 Study Room

1

Cultural 1

7:00–9:00 Antje Duvekot and Robby Hecht The Avalon, 40 E Dover Street, Easton, MD, United States

Friday

Oct 16, 2026

Family 1

6:00–9:00 Petals & Pumpkins Corah's Corner, 105 N Talbot Street, Saint Michaels, MD, United States

1

Cultural 2

5:30–7:30 Vision Board Collage with Studio Photo Portrait Session 9 S Harrison St unit 9a, Easton, MD, USA
9:00–4:00 Half-Hull Modeling Workshop 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States

Saturday

Oct 17, 2026

General 1

9:00–1:00 Fall into St. Michaels 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States

Family 1

11:00–3:00 OCC CommUNITY Fall Fest Oxford Community Center, 200 Oxford Rd, Oxford, MD 21654, USA

Cultural 4

1:00–4:00 The Met: Live in HD Macbeth by Giuseppe Verdi The Avalon, 40 E Dover St, Easton, MD 21601-3013, United States
6:00–9:00 OkSoberFest 100 Peachblossom Road, Easton, MD 21601
7:30–9:00 CREATIO EX NIHILO | Gabriela Montero 17 South Washington Street, Easton, MD, USA
9:00–4:00 Half-Hull Modeling Workshop 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States

Sunday

Oct 18, 2026

General 1

9:00–1:00 Fall into St. Michaels 308 Watkins Ln, Saint Michaels, MD, United States, Maryland 21663, 308 Watkins Ln, St Michaels, MD 21663-2114, United States

Cultural 1

9:00–4:00 Half-Hull Modeling Workshop 213 N Talbot St, Saint Michaels, MD, United States, Maryland 21663, 213 N Talbot St, St Michaels, MD 21663-2103, United States

Upcoming events near Chester