Here is our Chesapeake Bay events calendar. We built it from the hosts’ own pages. Dates change each year. So check before you go.
Quick answer: Our Chesapeake Bay events calendar: OysterFest at the Chesapeake Bay Maritime Museum in St. Michaels (November 7 in 2026), the museum’s Sea Glass festival (November 21) and Winter on the Chesapeake (December 12), and skipjack races off Deal Island every Labor Day weekend.
Contents
Fall and Winter 2026
| Date | Event | Where |
|---|---|---|
| November 7 | OysterFest | Chesapeake Bay Maritime Museum, St. Michaels |
| November 21 | Sea Glass and Coastal Arts Festival, Holiday Edition | St. Michaels |
| December 12 | Winter on the Chesapeake | St. Michaels |
Source: Chesapeake Bay Maritime Museum.[1][2]
OysterFest
OysterFest 2026 ran from 10 a.m. to 4 p.m. There was an oyster stew contest and live music. Kids had games, and boat rides were free. Adult tickets cost $22 online.[2] A cruise left from Annapolis to get there.[3]
Every Labor Day
Skipjack races are held each Labor Day weekend off Deal Island, in Somerset County.[4]
Check Before You Go
Dates and prices change each year. Check the host’s page.
Frequently asked questions
When is OysterFest in St. Michaels? In 2026 it was on November 7.
When are the skipjack races? Every Labor Day weekend, off Deal Island.
What events are at the Chesapeake Bay Maritime Museum? OysterFest, a sea glass festival and Winter on the Chesapeake, among others.
References
- [1] Chesapeake Bay Maritime Museum, Annual Festivals – last checked 11/08/2026
- [2] Chesapeake Bay Maritime Museum, OysterFest 2026 – last checked 11/08/2026
- [3] Watermark, Public Cruises in Annapolis and Baltimore – last checked 11/08/2026
- [4] Maryland State Archives, Maryland State Boat: Skipjack – last checked 11/08/2026
Find St. Michaels on our map.