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Chestertown Weekend 2023
Date: Friday, May 26, through Monday, May 29
Time: All Day
Baltimore Bike Club Presents the 39th Chestertown Weekend
Formerly Kent County Spring Fling
May 26-29, 2023
Enjoy riding along the flat, scenic roads of Kent County, Maryland
Stay in the historic port town of Chestertown, MD on the Chester River
- Rides for all levels and abilities from 10 to 100 miles
- Lodging at Washington College
- Plenty of fun for non-riders too!
- Excellent Cuisine: All meals provided from Friday dinner to Monday breakfast
, except for Saturday lunch
- Social Events: Block Party with live music, Ice Cream Social, Lawn Games, and Trivia Contest with prizes
- Enjoy the Annual Chestertown Tea Party Festival
- 3-day option available
- Inflation buster discounts available for early registration
Only 70 miles from Baltimore/DC, 85 miles from Philadelphia, and 170 miles from New York City.
We stay on the campus of Washington College in the historic port town of Chestertown.
- 3–4 rides everyday with ride leaders
- Over 20 other rides to choose from without ride leaders
- Routes will be available on Ride with GPS
- Helmets are mandatory
- Friday: Block Party at the waterfront 5-9 with live music
- Saturday Morning: Chestertown Farmers Market
- Saturday Morning: 5k run 8am
- Saturday evening: Local Homemade Ice Cream and Cornhole
- Sunday Lunch: b-b-q picnic at Worton park with veggie options
- Sunday Afternoon: 12–4 Local Beer Festival and live music (additional fee)
- Sunday Evening: Come test your wits at our Trivia Contest
- Throughout the weekend: Chestertown Tea Party Festival showcasing living history, music, crafts, parade, wacky boat races and local foods—a 10-minute walk from the college
- Standard double room with two single beds. Shared restrooms down the hall.
- Private Single Room additional $30. Shared restrooms down the hall.
- Upgrade to suite:
- Western Shore suites: four single bedrooms, 2 baths, and a living room-kitchenette
- Harford Suites: seven-person suites with 2 double rooms and 3 single rooms. Each suite has living room, full refrigerator, microwave and 2 baths
- Note: You will need to bring your own linens, towels, pillow, and toiletries
- Check-in: Friday noon–10pm
- Check-out: Monday before 3pm
Note: The 3-day event concludes after the picnic on Sunday.