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Events and Things to do in Chester, MD

Search for something you love or check out popular events in your area.

Maryland Commodity Classic 2026
Thu, Jul 23, 8:00 AM
Centreville · Queen Anne's County 4-H Park
Maryland Commodity Classic 2026
Thu, Jul 23, 8:00 AM
Centreville · Queen Anne's County 4-H Park
Carriages on West Street
Sun, Aug 9, 8:30 AM
Annapolis · Carriages on West Street
Carriages on West Street
Sun, Aug 9, 8:30 AM
Annapolis · Carriages on West Street
Dungeon BAR Crawler Carl
Sat, Jul 25, 1:00 PM
Annapolis · Latitude 38° Waterfront Dining
Dungeon BAR Crawler Carl
Sat, Jul 25, 1:00 PM
Annapolis · Latitude 38° Waterfront Dining
Almost full
Thomas Point Shoal Tour - Sunday, June 28th - 12:00 pm
Sunday at 12:00 PM
Annapolis · Dock Behind Annapolis Maritime Museum
Almost full
Thomas Point Shoal Tour - Sunday, June 28th - 12:00 pm
Sunday at 12:00 PM
Annapolis · Dock Behind Annapolis Maritime Museum
Almost full
Chart House Prime - Cakebread Cellars Wine Dinner
Thu, Jul 16, 7:00 PM
Annapolis · Chart House Prime
Almost full
Chart House Prime - Cakebread Cellars Wine Dinner
Thu, Jul 16, 7:00 PM
Annapolis · Chart House Prime
Hogs and Heroes Cash Bingo
Sun, Jul 19, 12:00 PM
Stevensville · American Legion Post 278
Hogs and Heroes Cash Bingo
Sun, Jul 19, 12:00 PM
Stevensville · American Legion Post 278
Krimson Tide: The Kritical Yacht Party of the Summer
Sat, Jul 18, 6:00 PM
Annapolis · 1 Dock St
Krimson Tide: The Kritical Yacht Party of the Summer
Sat, Jul 18, 6:00 PM
Annapolis · 1 Dock St
Curtains: A Musical Comedy Whodunit from The Talent Machine Co.
Sun, Jul 12, 2:00 PM
Arnold · Pascal Center for Performing Arts
Curtains: A Musical Comedy Whodunit from The Talent Machine Co.
Sun, Jul 12, 2:00 PM
Arnold · Pascal Center for Performing Arts
Sales end soon
Advanced Sex Offender Specialist Interview Course 2026
Tomorrow at 8:00 AM
Annapolis · The Westin Annapolis
Sales end soon
Advanced Sex Offender Specialist Interview Course 2026
Tomorrow at 8:00 AM
Annapolis · The Westin Annapolis
AACC Volleyball Summer Skills Clinics
Tue, Jul 7, 6:00 PM
Arnold · Jenkins Gymnasium
AACC Volleyball Summer Skills Clinics
Tue, Jul 7, 6:00 PM
Arnold · Jenkins Gymnasium
Sales end soon
Expansion: Creating Space for New Possibilities — Gazespotting, Meditation
Sunday at 10:00 AM
Pasadena · Dun-Pikin Farm
Sales end soon
Expansion: Creating Space for New Possibilities — Gazespotting, Meditation
Sunday at 10:00 AM
Pasadena · Dun-Pikin Farm
Sales end soon
Daphne Eckman Band, Dream Punch, Joy on Fire, and Noise Merchants
Friday at 7:00 PM
Annapolis · Metropolitan Kitchen & Lounge
Sales end soon
Daphne Eckman Band, Dream Punch, Joy on Fire, and Noise Merchants
Friday at 7:00 PM
Annapolis · Metropolitan Kitchen & Lounge
Amy Speace in Annapolis, MD
Wed, Jul 15, 8:00 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Amy Speace in Annapolis, MD
Wed, Jul 15, 8:00 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Sales end soon
Comedy Club Takeover at TGI Fridays Annapolis | Live Stand-Up Comedy Night
Thursday at 8:00 PM
Annapolis · TGI Fridays
Sales end soon
Comedy Club Takeover at TGI Fridays Annapolis | Live Stand-Up Comedy Night
Thursday at 8:00 PM
Annapolis · TGI Fridays
Going fast
3 week birth class series (AAMC) -IN PERSON
Tue, Jul 7, 4:30 PM
Annapolis · AAMC Belcher Pavilion
Going fast
3 week birth class series (AAMC) -IN PERSON
Tue, Jul 7, 4:30 PM
Annapolis · AAMC Belcher Pavilion
Sales end soon
Crafts and Coffee
Friday at 6:00 PM
Annapolis · Ceremony Coffee Roasters - Roastery
Sales end soon
Crafts and Coffee
Friday at 6:00 PM
Annapolis · Ceremony Coffee Roasters - Roastery
Mini Birth Class
Sat, Jul 11, 9:00 AM
Annapolis · AAMC - Clatanoff Pavilion
Mini Birth Class
Sat, Jul 11, 9:00 AM
Annapolis · AAMC - Clatanoff Pavilion
Almost full
In-Person Newborn Care
Sat, Jul 11, 10:30 AM
Annapolis · Belcher Pavilion
Almost full
In-Person Newborn Care
Sat, Jul 11, 10:30 AM
Annapolis · Belcher Pavilion
Sales end soon
LGBTQ Paint Night @ NEO PIZZA - Annapolis
Tomorrow at 6:00 PM
Annapolis · Neo Pizza & Taphouse
Sales end soon
LGBTQ Paint Night @ NEO PIZZA - Annapolis
Tomorrow at 6:00 PM
Annapolis · Neo Pizza & Taphouse
The Conference for Coaches 2026
Sat, Aug 8, 8:00 AM
Arnold · AACC Health and Life Sciences Building
The Conference for Coaches 2026
Sat, Aug 8, 8:00 AM
Arnold · AACC Health and Life Sciences Building

Trends in Chester

Explore more trends

Explore more trends

Frequently asked questions about Chester

What are the best events to attend?

According to Eventbrite, the best events are:

Maryland Commodity Classic 2026

Carriages on West Street

Dungeon BAR Crawler Carl

Thomas Point Shoal Tour - Sunday, June 28th - 12:00 pm

Which events are currently trending in Chester?

The trending searches this month in Chester are:

craft fairs near chester maryland

Which events are coming up?

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

Advanced Sex Offender Specialist Interview Course 2026

LGBTQ Paint Night @ NEO PIZZA - Annapolis

Comedy Club Takeover at TGI Fridays Annapolis | Live Stand-Up Comedy Night

Crafts and Coffee