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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

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.


  • 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

Special Events

  • 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

Lodging Options

  • 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.

Register Here!