September 3-4, 10 a.m.-5 p.m. — Labor Day Weekend Art Show and Sale

Sunset Anchorage by George HamiltonDate: Saturday, September 3, 2022 and Sunday, September 4, 2022 from 10 am to 5 pm.
Location: “Under the tent” at St. Luke’s UMC, 304 S. Talbot Street
Download a flyer HERE!

St. Michaels Art League Labor Day Weekend Show and Sale with Banner Sales and Artist Demonstrations

Come One, Come All to the BIG TENT ART SALE sponsored by the St. Michaels Art League, our biggest sale of the year, Labor Day Weekend, Saturday, September 3, 10-5 and Sunday September 4, 10-5, located in the heart of downtown at 304 S. Talbot Street on the lawn of the United Method Church. It is FREE and open to the public.

Painting by George Hamilton “Sunset Anchorage”

Banners 2021Talbot Street Banners Featured at SMAL Labor Day Show

Participating in the event will be 30 plus artists, including many award-winning artists, that will be showing their work in various mediums depicting local scenes, boating scenes, still life and more.
Additionally, many of the “Celebrate St. Michaels” banners that have hung on Talbot Street in previous years will be available for sale. You may even find the original artwork of the banner available!

Mark your calendars for this wonderful show of art for by members of the League. For more information visit or contact Jane Anderson at

The “Celebrate St. Michaels” event is funded in part by a grant from the Talbot County Arts Council with revenue provided by the Maryland State Arts Council.

September 10, 2022, 9 a.m.—Children’s Art Day

ChildrensArtDay-Young Artists for publicationSt. Michaels Art League Annual Children’s Art Day!

Date: Saturday, September 10, 2022
Time: 9 a.m. to noon

The St. Michaels Art League is sponsoring a free event for kids, “Children’s Art Day” on Saturday, September 10, 2022, 9am-12pm. The event takes place on the lawn of St. Luke’s United Methodist Church, 304 S. Talbot St., St. Michaels, Md. This event is open to all children K-8thgrade. The league will supply all materials needed: acrylic paints, panels, brushes, etc. Old clothes are suggested.

This event is funded in part by the Talbot County Arts Council, with revenues provided by the Maryland State Arts Council

September 30,2022 – October 2, 2022 —Mid-Atlantic Small Craft Festival XXXIX

MASCF_02CBMM_ModelExpo_01 copyDates: Friday- Sunday, September 30, 2022 – October 2, 2022, 10am – 5pm

Please note: Public dates for this event are now Friday & Saturday. Participant dates are still Friday – Sunday. Please check back for details. Admission is good for both Saturday and Sunday and is $15 for adults, $12 for seniors, $6 for children ages 6 to 17, and FREE for CBMM and children 5 and under. All museum exhibitions will be open throughout the event.

Location: Chesapeake Bay Maritime Museum

On Friday & Saturday, September 30, 2022 – October 1, 2022, the Chesapeake Bay Maritime Museum will host one of the nation’s largest gatherings of small boat enthusiasts and unique watercraft at the Mid-Atlantic Small Craft Festival XXXIX.

Hundreds of amateur and professional boatbuilders and enthusiasts come from all over the region to display their one-of-a-kind kayaks, canoes, and other traditional small craft.

Sailing skiffs, rowing shells, kayaks, canoes, paddle boats, prams, and one-of-a-kind boats will be on display and in the water throughout this family-oriented event. Small craft owners hailing from all over the country will also be available to share their knowledge and boating experiences with guests.

Scenic river cruises aboard the 1920 buyboat Winnie Estelle will be available Friday & Saturday, along with food, and beverages on Saturday.

Museum shipyard staff and Chesapeake Wooden Boat Builders School instructors will be on hand Saturday to offer boatbuilding workshops and maritime demonstrations. Beginning at 1 p.m. on Saturday, a lively Miles River race of small craft can be watched from the museum’s waterfront and docks. Festival-goers can also vote for their favorite boat, with the People’s Choice award and others announced among participants on Saturday evening. Visit CBMM HERE for more info!

For safety reasons, non-service dogs need to be kept home during the Mid-Atlantic Small Craft Festival and all CBMM festivals. Leashed dogs are only permitted during non-festival days.

September TBD, 10 a.m.—Kirkin’ o’ the Tartan

Date: Sunday, September TBD, 2022 at 10 a.m.
Location: Christ Church, Episcopal Parish

Don’t miss the pageantry of this great Scottish tradition.  Don your tartan and come join us!  Plan on meeting up at 10:00 AM to process in for the 10:15 AM Service. All are welcome to enjoy the service and listen to the bagpipe and drum selections. Ice Cream by Highland Creamery will follow immediately on the lawn.

Postponed—St. Michaels Concours d’ Elegance


Location: TBD
Date: September TBD, 2021

St. Michaels Concours d’Elegance Chairman, Luke L. Phipps below, announced that the St Michaels Concours d’ Elegance, will once again be held on the famously idyllic waterfront lawn of Inn at Perry Cabin by Belmond and the Chesapeake Bay Maritime Museum. Check back here, tickets go on sale June 1st.

Please join us for an elegant weekend of Grand Classic Motoring, fine wines and gourmet food, classic wooden speed boats, fashion, and casual elegance on Maryland’s Eastern Shore. St. Michaels is home to galleries and museums, award-winning dining and accommodations, luxurious spas, and an upscale collection of boutiques. Accessibility by car, boat and small plane make it ideal for long weekends for travelers from D.C., Baltimore, and Philadelphia, New York and beyond.

Now in its 14th year, the internationally acclaimed St Michaels Concours was in fact opened on the grounds of the Inn at Perry Cabin back in 2007 by Concours Founding Chairman George Walish, past GM of Rolls Royce of North America.

“The Inn’s historic and elegant nature”, says Phipps, “its beautiful 200-year-old gardens and its grandeur are the perfect backdrop for an event that has style at its core.” The Inn’s waterfront lawn and show field on Sunday will feature rare, pre-war (1900-1942) European and American coach-built automobiles as well as significantly important post-war (1946-1969) Sports Cars. A special class of previous Best in Show winners is being created and for the first time inclusion of a Classic Car Auction on Saturday sponsored by The Classic Motor Museum.

The St. Michaels Concours d’Elegance showcases the finest motorcars from around the world and is proud to announce Sonny Abagnale is the Honorable Chairman for 2018. It’s fair to say Abagnale knows something about motorcars, whether it’s collecting, selling, renting or racing them. The former stock car racer and stunt driver has a rather significant private collection, including a 1931 Pierce Arrow that was originally owned by Rose Kennedy. “It has her initials on the passenger door and the darkened windows are an early attempt at providing security during the Great Depression,” he says.

The former car dealer also has provided cars for several television shows and films, including “The Godfather.” “I still have a couple, including Sollozzo’s Buick Limited Touring Sedan.”

But elegant touring cars and roadsters, particularly Duesenbergs, are the cars Abagnale is most fond of.

“They are the best. They’re all hand-built,” he says. “I showed a 1934 Duesenberg SJ Rollston Limousine at Pebble Beach in 2014. It’s is all original and fully restored. With a supercharger and a closed roof, it’s very rare. The original owner had it built to tour Europe and carry 800 lbs. of luggage on the roof.”

The Duesenberg Limousine is representative of the qualities that collectors like Abagnale look for in classic automobiles — elegance, rarity and provenance — and when they are fully restored why collectors seek to present them at Pebble Beach, Amelia Island and other Concours events around the country such as the St Michaels Concours.

The Concours will continue its partnership with the Classic Motor Museum in 2018, too, with plans for the Museum to host Saturday’s Motoring Tour departing from the newly constructed post and beam exhibits barn housing the museum’s main collection.

Final details of Concours weekend are being made to include a Gala and Dinner Dance on Saturday evening at Inn at Perry Cabin to benefit the Classic Motor Museum’s budding educational program.

In the tradition of the historic Concours events held in Paris, Sunday’s exhibit of automobiles will be complemented by an enhanced and elegant fashion show. An additional display of classic wooden speed boats, along Inn at Perry Cabins waterfront lawn on the Miles River, will enhance the mood of stepping back in time.

Tickets will go on sale June 1, 2019 at

September TBD, 7:30 p.m.—Shakespeare in the Park

Shakespeare in the Park!
Directed by Kyler Taustin, Brown Box Theatre Project

ST. MICHAELS: Saturday, September TBD, 2022
Muskrat Park | 207 Willow Green Street

Free Outdoor Shakespeare returns! Performance begins at 7:30 p.m. and is free and open to the public. Bringing a chair or blanket is recommended.

For more details visit

This program is funded in part by the Town of St. Michaels, the Maryland State Arts Council and the Talbot County Arts Council.

TBD, 8:30 a.m.—Conversation with a Commissioner

Join Commissioner Mike Bibb for coffee and discussion of current projects, ideas, and citizen concerns.
Usually held on the third Saturday of each month at 8:30 a.m. in the Boy Scout Cabin at 407 St. Mary’s Sq.

October TBD—Christ Church Fall Rummage Sale

a8f4bbcd128d4a93a98ee7195a8efe56Dates: Donations will be accepted Monday, Tuesday & Wednesday, October TBD from 9 a.m. – 3 p.m. at the Parish House. SHOPPING HOURS: Friday from 7 a.m. to 2 p.m. and Saturday from 8 a.m. to 12 noon.
Location: Christ Church, Episcopal Parish

The time has come to clean out your closets, your attic, and your garage while giving back to our community. We are looking for furniture, kitchenware, and linens, gently used fall/winter clothing for women, men and children, shoes, jewelry, books, art work, and toys. And if that “special outfit” is no longer special, please donate to our women’s boutique. We are also looking for volunteers to join us in this fun and worthwhile event to assist during the week by accepting donations, setting up and organizing, providing lunch for the our hard working team, and working during the sale itself. We also encourage everyone to come and shop—you may find that hidden treasure! And remember, all proceeds from the sale are donated to charities assisting children, families and the elderly. For more information, contact Judy Sandground, 703-408-1890.

Fall Rummage Sale! THE MOVIE! Watch a fun video here!

October 12, 7 a.m.—Fire Department Flea Market

The Fall Flea Market will be Saturday, October 12, 2019 at the St. Michaels Fire Department. Doors open at 7 a.m. Rain or Shine, 75 tables of treasures, something for everyone, all under one roof! For more info, visit

October TBD, 1 p.m.—Annual Auction to benefit Fire Departments

Date: 38th Annual Volunteer Firefighters’ Auction, Sunday, October TBD, 1 p.m.- til
Location: Harrison’s Eastern Shore, 1216 S. Talbot Street

We are pleased to announce that the 39th Annual Volunteer Firefighters’ Auction will be held at Harrison’s Eastern Shore Restaurant. 100% of the proceeds of this auction will benefit the St. Michaels and Tilghman Island Volunteer Fire Departments. This is the largest fundraiser of the year for both departments, and it would not be possible without the generous donations that we receive from our local community partners. Our goal this year is to raise $70,000!

Please consider supporting our event by donating a gift certificate(s), merchandise, and/or a service(s). In addition to our traditional live auction, we are hoping to add a silent auction this year. All donations are greatly appreciated and are tax deductible. A receipt will be delivered to you when your item(s) is picked up.

A donation form for auction items is attached. Please complete the form and then call or email us and we will arrange a time that is convenient for you! We would like to receive all donations by Sunday, October 21st.

Thank you for your continued support! We hope to see you Sunday for food, fun, and fundraising!

Contact Jessica Boyd Kastel, Auction Committee Chairperson,