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Events and Things to do in Tolchester, MD

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30th & Final Chestertown Jazz Festival
Sat, Sep 12, 12:00 PM
Heron Point · Wilmer Park
30th & Final Chestertown Jazz Festival
Sat, Sep 12, 12:00 PM
Heron Point · Wilmer Park
2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm
Sat, Oct 31, 10:30 AM
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm
Sat, Oct 31, 10:30 AM
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm
Fri, Oct 30, 2:30 PM
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm
Fri, Oct 30, 2:30 PM
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm
Sun, Nov 1, 1:00 PM
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm
Sun, Nov 1, 1:00 PM
Heron Point · Chestertown Marina
2026 Sultana Downrigging Festival Music Village Passes
Heron Point · Chestertown Marina
2026 Sultana Downrigging Festival Music Village Passes
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm
Sat, Oct 31, 2:30 PM
Heron Point · Chestertown Marina
2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (afternoon),2:30pm-5:00pm
Sat, Oct 31, 2:30 PM
Heron Point · Chestertown Marina
CHICNIC - CHARM CITY PICNIC
Tomorrow at 2:00 PM
Canton · Canton Waterfront Park
CHICNIC - CHARM CITY PICNIC
Tomorrow at 2:00 PM
Canton · Canton Waterfront Park
Maryland Deathfest XXII
Thu, May 27, 3:00 PM
Oldtown · Baltimore, MD
Maryland Deathfest XXII
Thu, May 27, 3:00 PM
Oldtown · Baltimore, MD
2026 BBQ and Brews
Sat, Sep 5, 12:00 PM
Maryland · 7281 Wilkins Ln
2026 BBQ and Brews
Sat, Sep 5, 12:00 PM
Maryland · 7281 Wilkins Ln
All White & Demin Yacht Party Ft. Still Familiar
Tomorrow at 1:00 PM
Essex · 1901 Old Eastern Ave
All White & Demin Yacht Party Ft. Still Familiar
Tomorrow at 1:00 PM
Essex · 1901 Old Eastern Ave
Fly Society—Summer’s Last Blast Off
Thursday at 6:00 PM
Canton Industrial Area · Euphoria Night Club
Fly Society—Summer’s Last Blast Off
Thursday at 6:00 PM
Canton Industrial Area · Euphoria Night Club
Bmore Cleanup Crew: HIIT, Harbor Cleanup & Social
Tomorrow at 10:00 AM
Canton · Canton Waterfront Park
Bmore Cleanup Crew: HIIT, Harbor Cleanup & Social
Tomorrow at 10:00 AM
Canton · Canton Waterfront Park
The Cove Girls Drag Show: RuPaul's Drag Race Loosey Laduca
Sat, Sep 12, 6:00 PM
Saint Helena · The Cove
The Cove Girls Drag Show: RuPaul's Drag Race Loosey Laduca
Sat, Sep 12, 6:00 PM
Saint Helena · The Cove
Wine On The Water (R&B & Neo Soul) Wine & Arts Festival
Sun, Sep 13, 12:00 PM
Middle Branch/Reedbird Parks · Middle Branch Waterfront
Wine On The Water (R&B & Neo Soul) Wine & Arts Festival
Sun, Sep 13, 12:00 PM
Middle Branch/Reedbird Parks · Middle Branch Waterfront
ONE BIG RODEO (Baltimore)
Sat, Sep 12, 4:00 PM
Canton Industrial Area · Euphoria Night Club
ONE BIG RODEO (Baltimore)
Sat, Sep 12, 4:00 PM
Canton Industrial Area · Euphoria Night Club
ABM Glow & Cruise Yacht Party
Tomorrow at 5:30 PM
Essex · 1901 Old Eastern Ave
ABM Glow & Cruise Yacht Party
Tomorrow at 5:30 PM
Essex · 1901 Old Eastern Ave
Back to school community family fun day
Tomorrow at 2:00 PM
Madison-Eastend · Eager Park
Back to school community family fun day
Tomorrow at 2:00 PM
Madison-Eastend · Eager Park
Summer Colors Day Party featuring Tevin Campbell
Mon, Sep 7, 4:00 PM
Locust Point Industrial Area · Baltimore Museum of Industry
Summer Colors Day Party featuring Tevin Campbell
Mon, Sep 7, 4:00 PM
Locust Point Industrial Area · Baltimore Museum of Industry
WATA WUK: Foam | Water | Soca | Dancehall
Tomorrow at 2:00 PM
Downtown · Power Plant Live!
WATA WUK: Foam | Water | Soca | Dancehall
Tomorrow at 2:00 PM
Downtown · Power Plant Live!
Voices of History Street Fair
Sat, Sep 19, 11:00 AM
Oliver · The National Great Blacks In Wax Museum
Voices of History Street Fair
Sat, Sep 19, 11:00 AM
Oliver · The National Great Blacks In Wax Museum

1 of 500

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Frequently asked questions about Tolchester

What are the best events to attend?

According to Eventbrite, the best events are:

30th & Final Chestertown Jazz Festival

2026 Downrigging Tall Ship Sails: SATURDAY OCT 31 (morning), 10:30am-1:00pm

2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Bmore Cleanup Crew: HIIT, Harbor Cleanup & Social

All White & Demin Yacht Party Ft. Still Familiar

CHICNIC - CHARM CITY PICNIC

Back to school community family fun day

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