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Events and Things to do in Chester, MD

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Almost full
Ballet Theatre of Maryland Annual Conservatory Showcase 2026
Thu, May 28, 6:30 PM
Annapolis · Maryland Hall
Almost full
Ballet Theatre of Maryland Annual Conservatory Showcase 2026
Thu, May 28, 6:30 PM
Annapolis · Maryland Hall
10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival
Sat, May 30, 2:00 PM
Annapolis · Naval-Marine Corps Stadium
10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival
Sat, May 30, 2:00 PM
Annapolis · Naval-Marine Corps Stadium
American Voices United Through Song - June 6, 2026
Sat, Jun 6, 7:30 PM
Annapolis · Maryland Hall
American Voices United Through Song - June 6, 2026
Sat, Jun 6, 7:30 PM
Annapolis · Maryland Hall
Almost full
Dad Games Father's Day Fishing Derby and Brunch
Sat, Jun 6, 6:30 AM
Grasonville · 202 Wells Cove Rd
Almost full
Dad Games Father's Day Fishing Derby and Brunch
Sat, Jun 6, 6:30 AM
Grasonville · 202 Wells Cove Rd
Rock the Dock
Thu, Jun 4, 6:00 PM
Annapolis · Annapolis Maritime Museum & Park
Rock the Dock
Thu, Jun 4, 6:00 PM
Annapolis · Annapolis Maritime Museum & Park
The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sun, Jun 7, 4:45 PM
Annapolis · Annapolis City Dock
The Hip Hop R&B Yacht Party Annapolis MD 6.7.2026
Sun, Jun 7, 4:45 PM
Annapolis · Annapolis City Dock
Going fast
6/3/26 - Connecting w/ Your Loved Ones - Medium Debbie @ Annapolis Crystals
Wed, Jun 3, 12:30 PM
Annapolis · Annapolis Crystals
Going fast
6/3/26 - Connecting w/ Your Loved Ones - Medium Debbie @ Annapolis Crystals
Wed, Jun 3, 12:30 PM
Annapolis · Annapolis Crystals
Sales end soon
Northeast Regional Fellowship- Thrive Conference
Thursday at 7:00 PM
Annapolis · Crowne Plaza Annapolis, an IHG Hotel
Sales end soon
Northeast Regional Fellowship- Thrive Conference
Thursday at 7:00 PM
Annapolis · Crowne Plaza Annapolis, an IHG Hotel
Sales end soon
10th Anniversary TShirt
Saturday at 11:00 AM
Arnold · 613 College Pkwy
Sales end soon
10th Anniversary TShirt
Saturday at 11:00 AM
Arnold · 613 College Pkwy
Sagittarius Full Moon Circle & Crystal Grid Workshop with Donna & Audrey
Sun, May 31, 10:30 AM
Annapolis · Annapolis Crystals
Sagittarius Full Moon Circle & Crystal Grid Workshop with Donna & Audrey
Sun, May 31, 10:30 AM
Annapolis · Annapolis Crystals
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
Sun, May 31, 11:00 AM
Annapolis · Great Frogs Winery
Vino & Vinyasa with Lindsay Cook at Great Frogs Winery
Sun, May 31, 11:00 AM
Annapolis · Great Frogs Winery
Going fast
The Heather Pierson Duo in Annapolis, MD
Tomorrow at 7:30 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Going fast
The Heather Pierson Duo in Annapolis, MD
Tomorrow at 7:30 PM
Annapolis · 49 West Coffeehouse, Winebar & Gallery
Going fast
Chart House Prime - Duckhorn Wine Dinner
Thu, May 28, 7:00 PM
Annapolis · Chart House Prime
Going fast
Chart House Prime - Duckhorn Wine Dinner
Thu, May 28, 7:00 PM
Annapolis · Chart House Prime
PT. 2 ON THE WATER
Sun, Jun 14, 4:00 PM
Pasadena · Kurtz's Beach Ltd
PT. 2 ON THE WATER
Sun, Jun 14, 4:00 PM
Pasadena · Kurtz's Beach Ltd
Maryland Crop Scouting School at WYE
Thu, Jun 25, 9:00 AM
Queenstown · Wye Research & Education Center
Maryland Crop Scouting School at WYE
Thu, Jun 25, 9:00 AM
Queenstown · Wye Research & Education Center
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wednesday at 5:00 PM
Annapolis · 2000 Medical Pkwy
Going fast
In-person Lactation Basics - AAMC Annapolis, MD
Wednesday at 5:00 PM
Annapolis · 2000 Medical Pkwy
Almost full
In-Person Newborn Care
Sat, Jun 13, 10:30 AM
Annapolis · Belcher Pavilion
Almost full
In-Person Newborn Care
Sat, Jun 13, 10:30 AM
Annapolis · Belcher Pavilion
Going fast
Annapolis Kappas 11th Annual Bowling Bash
Sun, May 24, 8:00 PM
Annapolis · Annapolis Bowl
Going fast
Annapolis Kappas 11th Annual Bowling Bash
Sun, May 24, 8:00 PM
Annapolis · Annapolis Bowl
Light the Lamp for Liam
Sat, May 30, 3:00 PM
Easton · Talbot County Ice Skating Rink
Light the Lamp for Liam
Sat, May 30, 3:00 PM
Easton · Talbot County Ice Skating Rink
Going fast
Drag [Me To] Brunch at The Wildset!
Sun, Jun 7, 11:00 AM
Saint Michaels · 113 North St
Going fast
Drag [Me To] Brunch at The Wildset!
Sun, Jun 7, 11:00 AM
Saint Michaels · 113 North St

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:

Ballet Theatre of Maryland Annual Conservatory Showcase 2026

10th Annual Pints 4 Paws Homebrewing and Craft Beer Festival

American Voices United Through Song - June 6, 2026

Dad Games Father's Day Fishing Derby and Brunch

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:

The Heather Pierson Duo in Annapolis, MD

In-person Lactation Basics - AAMC Annapolis, MD

Northeast Regional Fellowship- Thrive Conference

10th Anniversary TShirt