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

Featured Events

October 5, 2024

dasbestoktoberfest.com

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

Over 150 Beers, wines and Schnapps highlight this all-you-care-to-taste German-themed extravaganza! Join in the Beer Games with your friends, dance with the live music and kick it up with the oompah bands!

October 12 - 13, 2024

concertsforcausesinc.org

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

Concerts for Causes Inc Presents Savor Bowie 2024 Food, Wine, and Music festival, Now 2 days! featuring Free admission (You heard right, Free Admission) and Complimentary Food and Wine tastings from the top wineries in the area. Vendors and Artisans, Antique and New Car display. Two Stages & many areas of music and other entertainment! Great kid's area! A non-profit organization raising funds to give musical instruments to students.

October 19, 2024

whiskeywinefire.com

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

An elegant evening in the Infield - this is an exclusive foodie celebration that features: Whiskey Bars, Elegant Wines and cocktails, great music, tented Food Stations, Food Trucks and restaurants, and Bonfires throughout. Relax around the fire gardens and enjoy an inspired take on fire-kissed BBQ, specialty grilling, and drink pairings. Enjoy the firebreathers and artists who set the night ablaze. Please dress appropriately, the event is outdoors. Souvenir glass to taste Whiskeys and wines and Food Galore! Enjoy great BBQ, grilled meat selections, and other goodies...Food Trucks, plus a S'mores station

October 26, 2024

wesleychapelurbana.com

(301) 662-5769
Urbana Vol. Fire & Rescue Company - Frederick, MD

Vendors will sell original crafts including jewelry, stained glass, woodworking, skin care, primitives, knitted and crochet, candles, fabric & textiles, floral, pottery, and seasonal crafts, artwork in several mediums and photography. Breakfast, lunch and bake table provided by the Church ladies of Wesley Chapel.

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.

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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.