St. Michaels Events



Wylder Hotel Tilghman Island

2019 Happenings Calendar

Concert Series


Crab illustration

Monday April 1st: Crab Season Begins

Friday April 5th 5 – 7 pm: Gerry Mack live at Tickler’s

Saturday April 6th & Sunday 7th: St. Michaels Sea Glass Festival

Thursday April 11th – Saturday April 13th: Talbot County Restaurant Week. 3-Course Prix Fixe Menu Dinner Special at Tickler’s Thur – Sun, $35.19* Per Person

Friday April 12th 7 – 9 pm: Kenny Haddaway Live in Concert at Tickler’s

Saturday April 13th: Restaurant Week Lunch Special 2-Course Prix Fixe Menu $20.19* Per Person

Saturday April 13th 3-6pm: NOW FULL Stained Glass Mosaic Art Workshop with Local Artist Jen Wagner, $60 + Enjoy Food & Drink Specials

Friday April 19th – Sunday April 21st: Tulip and Wine Package Add-On Available for Overnight Stays

Friday April 19th – Sunday April 21st: Easter Weekend 3-Course Dinner Menu All Weekend Long – Replaces Regular Menu

Friday April 19th 5 – 7 pm: Joe Hickey Live in Concert at Wylder

Saturday April 20th – Wednesday May 15th: Striped Bass Trophy Season

Friday April 26th 5 – 7 pm: Gerry Mack Live in Concert (Free Onsite Concert)

Saturday April 27th & Sunday April 28th: St. Michaels Wine Fest

*Not including tax, gratuity and beverages.



Thursday May 2nd– Sunday May 5th: Cinco De Mayo Dinner & Drink Specials in Tickler’s Restaurant

Saturday May 11th: Mother’s Day Family Style Dinner Specials

Sunday May 12th 2 – 4 pm: Joe Hickey Plays Live and Mother’s Day Weekend Brunch at Wylder

Sunday May 12th: Mother’s Day Brunch Features and Wine and Tulip Room Special

Saturday May 18th 3 – 5 pm: Gerry Mack Live in Concert (Free Onsite Concert)

Saturday May 18th: St. Michael’s Running Fest with Early Riser’s Running Breakfast Features

Thursday May 23rd – Monday May 27th: Memorial Day Weekend, Backyard Cookout, Pool Party and Summer Concert Series Kickoff


Saturday June 1st: St. Michaels Brew Fest

Sunday June 2nd 1 – 3 pm: Gerry Mack Live in Concert (Free Onsite Concert)

Saturday June 8th: Summer Concert Series

Friday June 14th – Sunday June 16th: CBMM Classic Boat Show & Father’s Day Weekend Fishing Charters (book before they are filled!)

Friday June 14th 7 – 9 pm: Joe Hickey Live in Concert for Father’s Day Weekend

Sunday June 16th: Father’s Day Backyard Cookout

Friday June 28th: Summer Concert Series



Thursday July 4th – Sunday July 7thIndependence Day Weekend Pool party, Backyard Cookout and Summer Concert Series

Sunday July 14th 2 – 4 pm: Joe Hickey Live in Concert at Wylder

Sunday July 14th – July 21st :  Plein Air Festival Tilghman Island Day Art Show & Reception

Saturday July 20thTilghman Island Seafood Festival & Summer Concert Series

Saturday July 27th 3 – 6pm: Justin Lees Jazz Trio Performs Live



Friday August 16th: Summer Concert Series

Thursday August 29th – Monday September 1st: Labor Day Weekend, Backyard Cookout, Summer Concert Series, Pool Party


Wylder Friends Header Image

Friday September 13th: Fall Concert Series



Saturday October 19th: Tilghman Island Day, Fall Concert Series

Thursday October 31st: Halloween



Thursday November 7th – Sunday November 10thWaterfowl Festival Weekend

Stay In Touch

Stay in touch.