Tilghman Island Annual Events Mark Your Calendar

Tilghman Island Seafood Festival - Held Saturday July 21st 11am to 6pm
Seafood, food vendors, arts and crafts, crab race, crab picking contest and firemens parade. Live music by "Southbound" Band. (For the benefit of the Tilghman Island Volunteer Fire Department.)
Tilghman Island Day Held the 3rd Saturday in October
Entire island village hosts a fun filled day of events. Watermans exhibit and Chesapeake Bay seafood. Music, auction, and boat docking contests too. Acres of memorabilia is for sale throughout the island. (For the benefit of the Tilghman Island Volunteer Fire Department.)

Visitors enjoy a beautiful vantage point for boat races along Tilghman-On-Chesapeake's picnic and yacht club grounds! View Skipjack and workboat races from Avalon Island at Tilghman On Chesapeake.
Waterfowl Festival
Waterfowl Festival, A wildlife arts festival. Enjoy a weekend festival featuring paintings, sculpture, carvings, decoys, duck stamps, photography, crafts, collectibles, demonstrations, music, food and much more! Free brochure, call

For more information about Talbot County attractions, call the Conference and Visitors Bureau at 410-822-4606.

For more information about St. Michaels, Maryland, visit their website at
Some Annual Events Held At Tilghman On Chesapeake
TAYA and the Kayak Rally

The rally is open to kayaks, paddle boards and canoes. Participants depart from Tilghman on Chesapeake’s Yacht Club and paddle 2.5 miles to Black Walnut Point Inn for a picnic lunch. After lunch there is an option for experienced paddlers to continue on and circumnavigate Tilghman Island or participants could take advantage of complimentary transportation for both themselves and their kayaks back to Tilghman on Chesapeake’s Yacht Club. Taya "Tilghman Area Youth Association" is a wonderful non profit program supporting kids and family fun .. to learn more visit their website at

Challenge Walk MS Chesapeake Challenge

Tilghman On Chesapeake is proud to be a host of the 'Challenge Walk MS: Chesapeake Challenge' to raise awareness and support to this 2 day, 30 mile, walking event. The walk included mid-shore counties. Walkers were in the Tilghman Island area and here at Tilghman On Chesapeake (T-O-C) for a rest stop. If you would like to learn more about MS Walks and Events call 443-641-1207 or visit online at

Remote Control Sailing

TOC has an RC enthusiast and resident who also serves as Secretary of RC Laser Class of North America. The event hosted the Remote Control Sailing races including replicas of the J Class boats that sailed for the Americas Cup in the the 1930's, and (shown) East Coast Twelve meters that resemble the Am Cup boats in the 60's. The RC boats were so fun to watch as they navigated their racing course. The group of racers also enjoyed watching the the first race of the Am Cup in the TOC Yacht Club after their three day event.

From the Bridge
Welcome from beautiful Tilghman Island, on Maryland's Eastern Shore of the Chesapeake Bay.
Thank you for visiting our site. We hope you’ll find time to come see us. If you are thinking about a waterfront community with good access to the Chesapeake Bay, you won’t be disappointed. Everyone that visits comments on what a beautiful spot this is here. And it is a fantastic boating location. Our homeowners love it. My favorite statement to newcomers is: “If you don’t like the beauty of our community and yacht club, I just can’t help you”.

The real estate business is coming back with a vengeance. Home sales are the best in ten years. Low interest rates are driving the strongest market in recent memory. Most resales have sold. The community has never looked better. Residents here take so much pride in their homes and lawns, that it is always a treat just to drive through.


I recently received a call from a neighboring community homeowner, asking to see a copy of our landscaping regs, as their owners were not keeping up. My reply was, that all of the beautiful landscaping and lawns are a direct result of the pride that our owners have.


2017 at the pool was almost perfect, with many continuous sunny days. I had a boating visitor to the marina remark that "This is the only place that we've ever been that looks like the picture." If you haven't seen our lovely island, you will be impressed. The weather was so nice, that our pool stayed open until late September.

We are hoping for another great boating season in 2018! (2017 was the best boating season we've had in decades.) Last summer, our sailing, cruising and fishing was fantastic. This past Spring, Stripers (Rockfish) appeared in late April, and it was a rare day that one of our folks didn't bring in a fish over 20 pounds. Several fish were caught over 40 pounds. Smaller stripers ensued. Nice Fall season as well. Some big Rockfish. We have a special rate for fishermen in the marina for the Spring season.

Three of my grandkids and I caught and released over 25 fish one afternoon, just 4 miles from the marina in the river. Many were close to 2 lbs. Crabbing was excellent in 2017. Best crabbing in years and the biggest crabs. Boaters catch crabs and big white perch right at the dock.


All in all, 2018 should be another great year in paradise. We hope to see you. Please call ahead for slip and homes' availability.


Bill Davis

© 2018 Tilghman on Chesapeake. All Rights Reserved.