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Festivals in Chestertown, MD.
Festivals, Reenactment Events, Art Shows

Featured Events

December 12 - 30, 2024

mdholidaylights.com

(800) 830-3976
Maryland State Fairgrounds - Infield - Timonium, MD - Timonium, MD

Capture the Magic...Create a New Holiday Tradition at the new outdoor Maryland Holiday Light Spectacular - see over a million beautiful lights and dozens of displays on a half-mile walking trail. See larger than life holiday scenes, wonderful music throughout and oversized snow globes. There will be magical interactive wand elements throughout the event, Children's Activities, a Moon Bounce a Holiday Village complete with Boutiques, Shops and Rotating Food Trucks and so much more!

December 13 - 15, 2024

(301) 643-9158
Charles County Fair Grounds - Laplata, MD

Christmas market with 175 crafters. We light up the fairgrounds with thousands of lights. Santa comes to town on a fire truck. There is a live nativity, Live Entertainment a kid's area, and Fireworks on Saturday. All spaces for Bakers, Candy makers, and Soap makers inside are full.

April 19 - 20, 2025

ConcertsforCausesinc.org

(301) 332-8318
Bowie Town Center - Bowie, MD

Complimentary Wine tastings! Great Food Vendors, Exhibitors, and Artisans. Many areas of music and other entertainment!

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Events in Chestertown, MD — upcoming

Chestertown Tea Party Festival
May 2025 (dates not updated)

Chestertown Tea Party Festival

Historic District, Chestertown, MD

Status: Updated 10/6/2023

A Festival organized by Chestertown Tea Party Festival, Inc..
This Maryland Festival will have crafts and fine craft exhibitors, and 25 food booths. There will be 2 stages with Regional talent and the hours will be Fri 5:30pm-9pm, Sat 9am-4pm, Sun 11am-4pm. This event will also include: non-motorized parade, re-enactment, 5 & 10 mile run, games, local wine and craft beer.