St. Michaels Wine Tasting Cruise!

St. Michaels Sailing Charters | 101 N Harbor Rd, St Michaels, MD

Your Wine Tasting ExperienceDiscover a truly unforgettable wine tasting cruise on the Chesapeake Bay. After boarding, youll set sail from historic St. Michaels and enjoy the gentle Bay breezes as…

Other Upcoming Events

OCT 27

Poplar Island Tours

We are excited to offer the members of the Talbot Historical Society a personal tour of Poplar Island again…

OCT 29 – OCT 30

Stillhouse Junkies

“Stillhouse Junkies make a mighty big joyful noise for a trio! There is some really fine pickin’ and songwr…

OCT 29 – NOV 1

Ravenscroft

Ravenscroft is coming to Tred Avon Players Community Theatre in Oxford, MD for an unforgettable event

OCT 31

Historic Drawbridge Running Festival

Please use the links for any updates to this event. We can't wait to show off one of Maryland's FLATTEST co…

NOV 6

Jake Shimabukuro

The Jimi Hendrix of the ukulele! Tickets: $50 (fees not included) Jake Shimabukuro is a world-renowned ukul…

NOV 7

CBMM's OysterFest

CBMM will host OysterFest on Saturday, Nov. 7, from 10am-4pm, inviting the community to celebrate the Bay’s…

AUG 2 – DEC 21

Happy Sunday at Theo's

Extend your weekend at Theo’s with Happy Sunday, featuring signature bites, sips, and Chef's Selections. En…

NOV 12 – NOV 15

Waterfowl Festival Premier Night Tickets

Experience the Waterfowl Festival at its finest with VIP access. This elevated ticket includes everything i…

NOV 21

Eastern Shore Sea Glass & Coastal Arts Festival: Holiday Edition

CBMM gets in the festive spirit, hosting the Holiday Edition of the Eastern Shore Sea Glass & Coastal Arts…

AUG 2 – NOV 22

Family Funday Sunday

CBMM is bringing fun to the end of your weekend with Family Funday Sundays presented by PNC Bank!\n

NOV 28

The Agitators at Carpenter St. Saloon

We're rolling back into town for another rocking night in St. Michaels with all the gang at C-Street! Kicki…

NOV 28

Shop Small Saturday

Save the date for Shop Small Saturday! Start the holidays off right and support our local merchants!

DEC 5

Medium Debbie Wojciechowski

Medium Debbie Wojciechowski is back for TWO NIGHTS at the Stoltz to share her extraordinary abilities! *Ple…

DEC 5

Jazz on the Stage at OCC: Dominick Farinacci & Friends

A Talbot County favorite, we are excited to keep the Holiday tradition alive welcoming Dominick Farinacci b…

DEC 5

The Met: Live in HD Samson et Dalila by Camille Saint-Saëns

*TICKET SALES OPEN 10:00 AM ON JULY 22* RevivalBy Camille Saint-Saëns **The Met: LIVE in HD package – Purch…

DEC 5 – DEC 6

Easton's Holiday Parade

Hope you’re ready for some holiday cheer! Easton’s holiday parade will take place on December 5th, 2026. Wi…

DEC 6

Medium Debbie Wojciechowski

Medium Debbie Wojciechowski is back for TWO NIGHTS at the Stoltz to share her extraordinary abilities! *Ple…

DEC 11 – DEC 13

Oxford Holiday Market

Spend a December Weekend in Oxford: Holiday Market Returns to Eastern Shore Village for Third Year The Oxfo…

DEC 11 – DEC 13

Oxford Holiday Market 2026

In its third year, this great shopping event showcases over 24 local artisans and makers along with a visit…

DEC 11 – DEC 13

Christmas in St. Michaels, Maryland | Enjoy our historic waterfront town!

(Important Scam Note: We do not solicit vendor opportunities and tickets are not needed for the majority of…

DEC 12 – DEC 13

Winter on the Chesapeake at CBMM

You’re invited to experience Winter on the Chesapeake at the Chesapeake Bay Maritime Museum on Saturday, De…

JAN 23

The Met: Live in HD La Fanciulla del West by Giacomo Puccini

*TICKET SALES OPEN 10:00 AM ON JULY 22* New ProductionBy Giacomo Puccini **The Met: LIVE in HD package – Pu…

FEB 3 – FEB 7

Residency at Chesapeake Music Festival

MAR 20

The Met: Live in HD Silent Night by Kevin Puts & Mark Campbell

*TICKET SALES OPEN 10:00 AM ON JULY 22* New Production/Met PremiereMusic by Kevin Puts/Libretto by Mark Cam…

APR 3

The Met: Live in HD Manon by Jules Massenet

*TICKET SALES OPEN 10:00 AM ON JULY 22* RevivalBy Jules Massenet **The Met: LIVE in HD package – Purchase 8…

APR 24

The Met: Live in HD Otello by Giuseppe Verdi

*TICKET SALES OPEN 10:00 AM ON JULY 22* RevivalBy Giuseppe Verdi **The Met: LIVE in HD package – Purchase 8…

JUN 5

The Met: Live in HD Parsifal by Richard Wagner

*TICKET SALES OPENS 10:00 AM ON JULY 22* RevivalBy Richard Wagner **The Met: LIVE in HD package – Purchase…

Nearby Places to Explore

5 miles range

No nearby places found for this filter.