Chestertown Weekend 2023, May 26th-29th

Formally Kent County Spring Fling

Sponsored by the Baltimore Bike Club


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



Convenient location

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.


·         There will be 3- 4 rides everyday with ride leaders

·         There are also over 20 other rides to choose from without ride leaders

·         Routes will be available on Ride with GPS

·         Helmets are mandatory

Special Events

·         Friday- Block Party at the waterfront 5-9 with live music

·         Saturday Morning Chestertown Farmers Market

·         Saturday Morning 5k run 8am

·         Sat 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- a 10-minute walk from the college….. living history, music, crafts, parade, wacky boat races and local foods.        

Lodging Options

·         Standard double room with two single beds. Shared restrooms down the hall.

·         Private Single Room additional $30. Shared restrooms down the hall.

·         Optional lodging 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 till 10 PM

Check-out:Monday by 3 PM

Note: 3-day event ends after the picnic on Sunday.


Click Here To Register


COVID: We will be following the standard COVID protocols required by Washington College and Kent County.