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Chestertown
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64°F
Popular Events in Chestertown, MD
Dec
5
Dickens Victorian Tea
Dec 05, 2026 01:00 PM - 03:00 PM
Christ United Methodist Church
61.60 USD
Nov
21
Paint & Sip
Nov 21, 2026 02:00 PM - 06:00 PM
Sumner Hall
65.87 USD
Nov
15
Dan Paisley & The Southern Grass
Nov 14, 2026 07:00 PM - 09:00 PM
Chestertown Volunteer Fire Co
28.52 USD
Nov
7
Reiki Level 1 Training with Fletcher Johnson
Nov 07, 2026 07:00 AM - Nov 08, 2026 11:00 AM
400 S Cross St
Dec
5
Dickens Holiday Home Tour
Dec 05, 2026 10:00 AM - 03:00 PM
The Bank
49.87 USD
Nov
19
Sustainable Farming
Nov 19, 2026 06:00 PM - 08:00 PM
Sultana's Holt Center
Free
Dec
3
Friends Holiday Wreath Making Workshop
Dec 03, 2026 12:30 PM - 02:30 PM
343 High St
Nov
8
Learn to Play American MahJong-A 3 Part Series: Nov. 8, 15, 22
Nov 08, 2026 11:00 AM - 02:00 PM
Lawrence Wetlands Preserve
Free
Nov
7
Botanical Blues: Cyanotype
Nov 07, 2026 08:00 AM - 10:00 AM
343 High St
Nov
7
Bi-Monthly Bluegrass Jam
Nov 07, 2026 01:00 PM - 03:00 PM
Lawrence Wetlands Preserve
Free
Chestertown, MD · Latest Local
Events
Upcoming
Weekend
New
Nov
7
Reiki Level 1 Training with Fletcher Johnson
Nov 07, 2026 07:00 AM - Nov 08, 2026 11:00 AM
400 S Cross St
Nov
7
Botanical Blues: Cyanotype
Nov 07, 2026 08:00 AM - 10:00 AM
343 High St
Nov
7
Bi-Monthly Bluegrass Jam
Nov 07, 2026 01:00 PM - 03:00 PM
Lawrence Wetlands Preserve
Free
Nov
8
Jerry's 21st Annual Fall Car Show
Nov 08, 2026 03:00 AM
1940 E Joppa Rd
Nov
8
Michael Jackson Musical Bingo/Trivia Game Night
Nov 07, 2026 07:00 PM - 09:30 PM
The Greene Turtle Sports Bar & Grille
0.00 USD - 14.91 USD
Nov
7
MD 16 CE & IRS AFSP - Silver Spring, MD Saturday 9:30-12:30pm Fee: $240
Nov 07, 2026 05:30 AM - 08:30 AM
Montgomery College
Free
Nov
8
Inspire Ministries!
Nov 08, 2026 06:30 AM
8975 Old Guilford Rd suite 170
Free
Nov
6
Sapphic Speed Dating @ Olde Mother Brewing Co.
Nov 06, 2026 06:15 PM - 09:30 PM
Olde Mother Brewing
17.85 USD
Nov
7
Winslow: An Evening of the Eagles
Nov 06, 2026 08:00 PM - 10:00 PM
Live At Hub City Vinyl
35.71 USD - 51.14 USD
Nov
6
2026 Mountain Maryland Film Festival
Nov 06, 2026 06:00 PM - Nov 07, 2026 09:00 PM
Frostburg Palace Theatre
15.00 USD - 25.00 USD
Nov
6
Field and Tide: A Culinary Festival at The Wildset
Nov 06, 2026 06:30 PM - 09:00 PM
113 North Street
113.89 USD - 273.95 USD
Nov
6
Holiday Ceramic Sip & Paint Night at WhataBoba Lusby
Nov 06, 2026 05:30 PM - 07:30 PM
232 Town Square Drive
10.91 USD - 55.20 USD
Nov
7
WE Back DOWN DaSHORE - The HC WEEKEND TAKEOVER
Nov 06, 2026 07:00 PM - 11:30 PM
Princess Anne Civic Center
33.85 USD - 402.00 USD
Nov
6
Skitzo Calypso with Son of Avery, Letterbox, Warren Under Water
Nov 06, 2026 06:30 PM - 11:30 PM
Main Street Tower
14.64 USD - 17.85 USD
Nov
6
Not Your YiaYia's Bingo! 2026
Nov 06, 2026 06:00 PM - 09:30 PM
Saint Demetrios Greek Orthodox Church GOYA
40.00 USD
Nov
6
Purrs and Pints: A Chesapeake Feline Association Music Bingo Fundraiser
Nov 06, 2026 06:30 PM - 09:00 PM
Hopkins Farm Brewery
14.64 USD
Nov
7
Off The Wall: 50th Year Reunion Show
Nov 06, 2026 08:00 PM - 11:00 PM
The Collective - Encore
33.62 USD
Nov
7
Black & White Noir Nights Masquerade Ball
Nov 06, 2026 08:00 PM - 11:55 PM
Bulle Rock Golf Course
108.55 USD
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