Upcoming Chester Events

Check out what's happening all around Chester, MD

Santa is Coming to Town at sweetFrog Kent island!

 Sat, 13 Dec at 01:00 pm sweetFrog Kent Island Free

Festive Finds Holiday Crafting Workshop

 Fri, 12 Dec at 06:00 pm 1545 Postal Road Chester MD

December's Finger-Paint Party at sweetFrog Kent Island

 Sat, 13 Dec at 11:00 am 200 Abruzzi Dr USD 13

Jazz In The Sanctuary

 Sat, 13 Dec at 05:00 pm 100 Union Wesley Cir, Chester, MD, United States, Maryland 21619

The Last Laugh of 2025 - Comedy Night

 Sat, 13 Dec at 07:00 pm Cult Classic Brewing Company

Words of the Prophets

 Sat, 24 Jan at 08:00 pm Cult Classic Brewing Company

Santa's Secret: Handmade Vendor Fair

 Sat, 20 Dec at 12:00 pm Cult Classic Brewing Company

Ashley and Rohry's Wedding AFTERPARTY

 Sat, 03 Jan at 06:00 pm Cult Classic Brewing Company

Free Kids Craft Making Edible Houses at sweetFrog Kent Island

 Fri, 12 Dec at 05:00 pm sweetFrog Kent Island Free

Bluegrass Nutcracker 2025 LIVE at Cult

 Fri, 19 Dec at 07:00 pm Cult Classic Brewing Company

sweetFrog Kent Island Story Time

 Tue, 09 Dec at 12:00 pm sweetFrog Free

Penguin Cupcakes - Caregiver & Me Cooking Class (Ages 2-8)

 Sat, 27 Dec at 11:00 am Taste Buds Kitchen - Kent Island - Chester (Chester, MD)

Free Holiday SWAPS craft at sweetFrog Kent Island

 Sat, 20 Dec at 12:00 pm sweetFrog Kent Island Free

Hot Cocoa Sip & Shop with Bella Jewel Boutique

 Fri, 19 Dec at 06:00 pm 1545 Postal Rd, Chester, MD 21619-2255, United States

Centreville Elementary School Mobile Spirit Night

 Wed, 17 Dec at 05:00 pm 1845 Main St, Chester, MD 21619

Tornado Rose / Seth Mitchell Band LIVE at Cult

 Fri, 27 Mar at 07:00 pm Cult Classic Brewing Company

THE WHOLE STINKIN' 2025: TRIVIA

 Fri, 02 Jan at 06:00 pm Cult Classic Brewing Company

2025 DUMPSTER FIRE

 Wed, 31 Dec at 06:00 pm Cult Classic Brewing Company

Songwriter Showcase w/ Sweet Leda, Callum, Kavoossi, Wordslave, and Joe Greene

 Fri, 26 Dec at 06:00 pm Cult Classic Brewing Company

December's Paint Party at sweetFrog Kent Island

 Sun, 14 Dec at 01:00 pm sweetFrog Kent Island USD 23

Books & Beers 2025

 Tue, 09 Dec at 06:00 pm Cult Classic Brewing Company

Sweet Cookies, Straight Talk

 Mon, 15 Dec at 05:00 pm Realty Navigator Kent Island, Broker Petra Quinn Free

Jingle & Mingle Holiday Craft Party

 Tue, 09 Dec at 06:30 pm El Jefe Mexican Kitchen/Tequila Bar

Avoid the Leak: Strategies for Pelvic Health

 Tue, 16 Dec at 01:00 pm K. Hovnanian's Four Seasons at Kent Island - Single Family Free

SweetFrog Homeschool Field Trip

 Fri, 09 Jan at 10:30 am sweetFrog Premium Frozen Yogurt (Kent Island, MD)

Spaghetti & Meatballs Family Cooking Class Ages 6+

 Sun, 28 Dec at 11:00 am 800-D Abruzzi Dr, Chester, MD 21619

12/15 2nd Annual Drink & Decorate Cookie Mansion COMPETITION @ Dock House Restaurant

 Mon, 15 Dec at 06:30 pm Dock House Restaurant

Noon Year's Eve Party at sweetFrog Kent Island

 Wed, 31 Dec at 11:00 am 200 Abruzzi Dr USD 18

Medium Debbie Wojciechowski LIVE at Cult 2026

 Thu, 09 Apr at 07:00 pm Cult Classic Brewing Company

10th Annual Chesapeake Bay Motoring Festival set for June 6-7, 2026 on Kent Island

 Sat, 06 Jun at 11:00 am Kent Island Yacht Club

Heart-Shaped Biscuits

 Sat, 14 Feb at 06:30 am 1845 Main St, Chester, MD 21619

Playing with Dixon Hall Band at The Jetty

Sat, 13 Dec at 03:00 pm The Jetty

Game Night

 Fri, 17 Apr at 06:00 pm The Church of Jesus Christ of Latter-day Saints

Game Night

 Fri, 20 Feb at 06:00 pm The Church of Jesus Christ of Latter-day Saints

Game Night

 Fri, 16 Jan at 06:00 pm The Church of Jesus Christ of Latter-day Saints

Game Night

 Fri, 19 Dec at 06:00 pm The Church of Jesus Christ of Latter-day Saints

Game Night

 Fri, 15 May at 06:00 pm The Church of Jesus Christ of Latter-day Saints

Game Night

 Fri, 20 Mar at 06:00 pm The Church of Jesus Christ of Latter-day Saints

Dinner with Santa Cow

 Wed, 10 Dec at 05:00 pm 1845 Main St, Chester, MD 21619

Family Game Night at sweetFrog Kent Island

 Thu, 16 Jan at 05:00 pm sweetFrog Kent Island USD 20