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Events and Things to do in Chester, MD

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Almost full
Maryland Crop Scouting School at WYE
Thursday at 9:00 AM
Queenstown · Wye Research & Education Center
Almost full
Maryland Crop Scouting School at WYE
Thursday at 9:00 AM
Queenstown · Wye Research & Education Center
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
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
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
Sales end soon
‘Just looking?’: Evaluating Risk in Online Behavior Course 2026
Monday at 8:00 AM
Annapolis · The Westin Annapolis
Sales end soon
‘Just looking?’: Evaluating Risk in Online Behavior Course 2026
Monday at 8:00 AM
Annapolis · The Westin Annapolis
Going fast
Chart House Prime - Cakebread Cellars Wine Dinner
Thu, Jul 16, 7:00 PM
Annapolis · Chart House Prime
Going fast
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
Sales end soon
Advanced Sex Offender Specialist Interview Course 2026
Wednesday at 8:00 AM
Annapolis · The Westin Annapolis
Sales end soon
Advanced Sex Offender Specialist Interview Course 2026
Wednesday at 8:00 AM
Annapolis · The Westin Annapolis
Almost full
Expansion: Creating Space for New Possibilities — Gazespotting, Meditation
Sun, Jun 28, 10:00 AM
Pasadena · Dun-Pikin Farm
Almost full
Expansion: Creating Space for New Possibilities — Gazespotting, Meditation
Sun, Jun 28, 10:00 AM
Pasadena · Dun-Pikin Farm
Daphne Eckman Band, Dream Punch, Joy on Fire, and Noise Merchants
Fri, Jun 26, 7:00 PM
Annapolis · Metropolitan Kitchen & Lounge
Daphne Eckman Band, Dream Punch, Joy on Fire, and Noise Merchants
Fri, Jun 26, 7:00 PM
Annapolis · Metropolitan Kitchen & Lounge
Going fast
Pure Comedy: Annapolis Stand Up Showcase
Today at 8:00 PM
Annapolis · Pure Boardshop
Going fast
Pure Comedy: Annapolis Stand Up Showcase
Today at 8:00 PM
Annapolis · Pure Boardshop
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
Sunset Floating Sound Bath with Artist Katie Detrich
Today at 6:45 PM
Pasadena · Cedarwood Cove Pool Association
Sales end soon
Sunset Floating Sound Bath with Artist Katie Detrich
Today at 6:45 PM
Pasadena · Cedarwood Cove Pool Association
Almost full
DMV R&B Wine Festival
Today at 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Almost full
DMV R&B Wine Festival
Today at 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Comedy Club Takeover at TGI Fridays Annapolis | Live Stand-Up Comedy Night
Thursday at 8:00 PM
Annapolis · TGI Fridays
Comedy Club Takeover at TGI Fridays Annapolis | Live Stand-Up Comedy Night
Thursday at 8:00 PM
Annapolis · TGI Fridays
Sales end soon
Afro - Soca Wine Music & Food Festival
Tomorrow at 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Sales end soon
Afro - Soca Wine Music & Food Festival
Tomorrow at 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
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
LGBTQ Paint Night @ NEO PIZZA - Annapolis
Wednesday at 6:00 PM
Annapolis · Neo Pizza & Taphouse
Sales end soon
LGBTQ Paint Night @ NEO PIZZA - Annapolis
Wednesday at 6:00 PM
Annapolis · Neo Pizza & Taphouse
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

Trends in Chester

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Frequently asked questions about Chester

What are the best events to attend?

According to Eventbrite, the best events are:

Maryland Crop Scouting School at WYE

Carriages on West Street

Maryland Commodity Classic 2026

Dungeon BAR Crawler Carl

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:

DMV R&B Wine Festival

Sunset Floating Sound Bath with Artist Katie Detrich

Pure Comedy: Annapolis Stand Up Showcase

Afro - Soca Wine Music & Food Festival