Kent County Maryland Calendar of Events- October 2024


Login to create a new event.      

October 1

Brampton Inn Ship-To-Shore Experience with Chester River Packet Co.
  • Brampton Inn Ship-To-Shore Experience with Chester River Packet Co.

  • Tuesday,   |  6:00pm - 8:00pm
  • Location: Brampton Inn - 25227 Chestertown Rd
  • The Brampton Inn invites visitors to catch the sunset aboard the Chester River Packet, a 1920’s-style, touring yacht. This immersive experience allows guests to mingle and unwind on a serene two...

    More information

October 5

Rock Hall FallFest
  • Rock Hall FallFest

  • Saturday,   |  10am-4pm
  • Location: Town of Rock Hall - Main Street Rock Hall
  • FallFest attracts thousands of visitors from across the eastern seaboard showcasing the quaint hamlet of Rock Hall as we celebrate our heritage as a waterman’s town. Locals and visitors alike at...

    More information

October 13

Chestertown Challenge Half Marathon & 5K Run/Walk
  • Chestertown Challenge Half Marathon & 5K Run/Walk

  • Sunday,   |  9:00am
  • Location: Wilmer Park - - Wilmer Park
  • Half Marathon & 5K Run/Walk to benefit KART, providing therapeutic horseback riding and equine activities for the special needs community.

    Both courses USAFT certified.

    Race day registrati...

    More information

October 17

Girls' Night Out on the River Packet
  • Girls' Night Out on the River Packet

  • Thursday,   |  6:00 - 8:00 pm
  • Location: River Packet - High Street Town Dock
  • Ladies' Night on the Chester River! Gather your friends/family for a fun evening with food and drinks aboard the River Packet. Reservations are required - click the link for more information and ...

    More information

Cars on High
  • Cars on High

  • Thursday,   |  6pm-8pm
  • Location: 300 Block of High Street
  • Come show off your favorite car or marvel at other people's pride and joy. This event does not require registration and is free and open to the public....

    More information

October 26

  • Harvest Celebration Dinner

  • Saturday,   |  6-9pm
  • Location: Crow Vineyard - 12441 Vansants Corner Rd
  • An annual tradition to host a celebration of the grape harvest with a family style dinner prepared by Celebrity Chef Robbie Jester, paired with Crow wines.

    $110...

    More information

2024 Betterton Cash & Bike Bash
  • 2024 Betterton Cash & Bike Bash

  • Saturday,   |  12pm - 5pm
  • Location: Betterton Vol. Fire Co. - 2 Howell Point Rd
  • Saturday Oct 26, 2024: Amazing afternoon of CASH giveaways & GRAND PRIZE giveaway of a BRAND NEW Harley Davidson Street Glide Motorcycle
    Doors will open at 11am & drawings begin @ 12pm
    Cash ...

    More information

Witches of Rock Hall - Saturday
  • Witches of Rock Hall - Saturday

  • Saturday,   |  11am - 4:30pm
  • Location: Town of Rock Hall - Ferry Park Beach and Main Street Rock Hall
  • Witches of Rock Hall weekend. Dancing, games, shopping, food, drinks and lots of witchy fun!!

    More information

October 27

Elegant Afternoon Tea at Brampton Inn
  • Elegant Afternoon Tea at Brampton Inn

  • Sunday,   |  2:00pm - 3:30pm
  • Location: Brampton Inn - 25227 Chestertown Rd, Chestertown MD 21620
  • Join us for an exquisite afternoon filled with charm and indulgence at Brampton Inn. Indulge in a delightful selection of finest teas and delectable treats that will transport you to a world of refine...

    More information