October 14—Second Saturday “Art Night Out”

Gravely Art Patrons at SMAL exhibitSt. Michaels Second Saturday “Art Night Out” In Fall of 2016, St. Michaels launched their monthly Second Saturday “Art Night Out” celebrations. The next Second Saturday is October 14th. Take a walking tour of St. Michaels’ six fine art galleries that are all centrally located on Talbot Street.


LOVE ART AND ST. MICHAELS?! Check out our Facebook Page “St. Michaels – Art Lives Here”

October 15, 1 p.m.—Annual Auction to benefit Fire Departments at Awful Arthur’s

Committee-PictureDate: Sunday, October 15, 1 p.m.- til
Location: Awful Arthur’s, 402 S. Talbot Street

Awful Arthur’s St. Michaels and the committee for the 37th Annual Firemen’s Auction are pleased to announce this year’s auction will be held on Sunday, October 15th, 2017 starting at 1:00pm at Awful Arthur’s. The event is open to the public and will feature live auctioneers and special food and drink items.

The committee is currently seeking donations for this year’s auction including donations of trips, services, art or other creative and unique items. Last year’s auction, the first for Awful Arthur’s, after 35 years at Carpenter Street Saloon was a huge success, raising over $73,000 with all proceeds benefitting the St. Michaels and Tilghman Volunteer Fire Departments.

To donate, please call event chairperson Donna Pierson at 410-822-5866.

Pictured: Josh Poore, Jeanne Bryan, Donna Pierson, Arthur Webb, Alan Faulkner, Terye Knopp, Keith Graffius, Julie Irimie, Marianne Yeager Stallsmith, Robin Harrison

October 21-22—Fall into St. Michaels

EventPhotoMini_Carpenter street halloweenAnnual Fall into St. Michaels has fun for all ages!

Events & Activities:
Fall into St. Michaels scheduled for the weekend of October 21-22, 2017
St. Michaels, Maryland

The change of the season brings excitement and vibrant color to the Town of St. Michaels, as residents and businesses celebrate their annual harvest festival “Fall into St. Michaels”.

pirate scarecrowThe Fall into St. Michaels festivities begin with the town-wide scarecrow contest on Saturday, October 14, 2017. Participating area businesses are competing in the Second Annual St. Michaels Scarecrow Contest, where each sponsoring business will have the chance to win first place in one of the following three categories: Traditional, Whimsical or Humorous and will seek the coveted People’s Choice award. Walk along the streets of St. Michaels, where you’ll find the scarecrows displayed in front of participating businesses and hung along the telephone poles on Talbot Street. Visitors can vote for the People’s Choice award online. The People’s Choice winner will be announced on Monday and can be seen on the “Visit St. Michaels” Facebook page and

kimThe following weekend, the Fall into St. Michaels festivities go into full swing on Saturday with the start of the Annual Pumpkin Carving Contest held at the St. Michaels Community Center early Saturday morning. Participating businesses sponsor the pumpkins, which are carved by experienced and novice carvers alike, each striving for the top spot in one of the four pumpkin categories. The pumpkins are judged from 1:00 p.m.-1:30 p.m. and then will remain on display until 7:00 p.m. on Saturday and 10:00 a.m. thru 2:00pm on Sunday.

pieThe Bay Hundred’s Annual Pumpkin Pie Competition will be held during the Pumpkin Carving Contest at the St. Michaels Community Center. The Pumpkin Pie Competition is open to professionals, home bakers and children. Each group will be judged on traditional or creative creations. Cash prizes will be awarded to top three winners in each category, and of course, bragging rights and a plaque go to the winners. Each contestant must submit 2-3 pies of the same recipe. The St. Michaels Community Center will be selling pieces and whole pies of those entered. Judging will begin at 10:00 am and sales will begin at 11:00am. Proceeds of the bake sale will benefit the programs and activities of the St. Michaels Community Center. Please contact Trish at the SMCC 410-745-6073 for more information or to register as an entrant. The St. Michaels Community Center is located on the corner of Railroad Street and Fremont Street.

Jack Russell RacesEvery year, dog owners from all over Maryland join the residents of St. Michaels on the lawn at the Inn at Perry Cabin for the annual Jack Russell Races. This year’s races are on Sunday, October 22nd and will begin at 11:00 am. Registration is available online on the event Facebook Page and at 10 a.m. that morning at the event. You can also register at St. Michaels Pet Supply, All Pets Veterinary Hospital and The Urban Pup. The proceeds from the benefit will go to the St. Michaels Community Food Pantry and Pet Pantries of Talbot, Caroline and Dorchester Counties. The races will be broken down into categories: Jack Russell, Dachshund Dash and the famous “So Your Dog Thinks He’s a Jack” race. All dogs are welcome at the event, big or small, racing or not, to mingle with other dog lovers in Talbot County. Dogs under 25 pounds are welcome to race. The event will be held, rain or shine! Refreshments, including Coffee & Donuts and a Bloody Mary & Mimosa Bar, will be available on-site. There will be live raffles of items from area restaurants and retailers between races! No Dog? No Problem- Fun for humans, too!

The St. Michaels Museum at St. Mary’s Square will offer one of their signature walking tours. The walking tour is $10 per person and also includes admission to the museum. Please visit the museum’s website for more information and to reserve your space:

Lastly, as a way to give back during the harvest months, the St. Michaels Business Association is combining their “Fall into St. Michaels” festivities with their Second Annual Food Drive for the St. Michaels Food Pantry. The St. Michaels Food Pantry, which is housed in Christ Church, is supported through individual food and financial contributions as well as donations from area businesses and organizations. It serves Talbot County residents requiring food assistance. A satellite program on Tilghman Island operates out of the Tilghman United Methodist Church. The St. Michaels Food Pantry also provides complete Thanksgiving and Christmas dinners to those in need. “Many members of our community struggle with providing healthy, nutritious food for their families. We hope our first annual food drive is the first of many to come that will help fill the shelves of the St. Michaels Food Pantry and help Talbot County residents in need.” said Kim Hannon, Secretary of the St. Michaels Business Association. While the St. Michaels Food Pantry appreciates every single food donation, they strive to offer a variety of food items that help balance nutritional intake, especially important to children, seniors, those with health challenges and those with culturally diverse diets. Drop off your donation items at the St. Michaels Community Center on Railroad Ave. during the hours of the Pumpkin Carving & Pie Baking contest.

Shop. Eat. Play. Stay – Visit St. Michaels or call 410.745.0411.

October 22, 10 a.m.—Jack Russell Races

Jack Russell FB headerDate: Sunday, October 22, 2017
Time: Registration at 10 a.m., Coffee & Doughnuts and a Bloody Mary & Mimosa Bar at 10 a.m., Races start at 11 a.m.
Location: On the lawn at the Inn at Perry Cabin
More info: Visit the Facebook Page
REGISTER your pup for the races! HERE

Every year, dog owners from all over Maryland join the residents of Talbot County St. Michaels on the lawn at the Inn at Perry Cabin for the annual Jack Russell Races. This year’s races will begin at 11:00 am. Registration is available online and at 10 a.m. that morning.

JRT pole signThe races will be broken down into categories: Jack Russell (flat and hurdles), Dachshund Dash and the famous “So Your Dog Thinks He’s a Jack” race. All dogs are welcome at the event, big or small, racing or not, to mingle with other dog lovers in Talbot County. Dogs under 25 pounds are welcome to race.

The event will be held, rain or shine! Refreshments, including Coffee & Doughnuts and a Bloody Mary & Mimosa Bar, will be available on site. There will be live raffles of items from area restaurants and retailers between races!

No Dog? No Problem- Fun for humans, too!

The proceeds from the benefit will go to Community Food Pantry and Pet Pantries of Talbot, Caroline, and Dorchester Counties. Want to make a donation? Buy a bone to be displayed on poles on Talbot Street! (see at left : ) Donate HERE

October 28—CBMM OysterFest

OysterFestDate: Saturday, October 28, 2017 — 
10 a.m.- 4 p.m.
Location: Chesapeake Bay Maritime Museum

Admission to OysterFest is $15 for adults, $12 for seniors,and $6 for children between the ages of six and 17. 
Children five years and under and CBMM members are admitted free. Food and boat rides are an additional cost. 
For more information, call 410-745-2916. Please leave your pets at home.

On Saturday, October 28, the Chesapeake’s oyster will be celebrated at the Chesapeake Bay Maritime Museum’s (CBMM) OysterFest in St. Michaels, MD. The event features live music oysters and other local fare, children’s activities, boat rides, oyster demonstrations, harvesting displays, retriever demonstrations, cooking demonstrations, documentary films, and an oyster stew competition among regional chefs.

TCWA volunteers will be serving freshly caught and shucked Chesapeake Bay oysters. Aquaculture raw oysters, steamed oysters, oyster fritters, and fried oyster sandwiches will also be available. For those who prefer to celebrate oysters rather than eat them, pit beef, hot dogs and hamburgers, along with cold beer, caramel apples, warm apple cider, and more will be offered. Festival-goers can take part in or just watch an oyster slurping contest, while others enjoy sampling oyster stew by local restaurants and chefs beginning at 11am and while the limited tastings last.

The stew competition takes place along the museum’s Fogg’s Cove side of campus, with bragging rights awarded to the chef who gets the most votes among participants. Local restaurants will also perform cooking demonstrations of signature oyster dishes throughout the day. OysterFest boasts plenty of family-friendly, educational, and fun waterfront activities designed to help kids to know how important the oyster is to the Chesapeake Bay. Families can play “Oyster Jenga,” explore an oyster nursery, participate in a scavenger hunt or face painting, or watch dip-net making and knot-tying demonstrations. Build-aboat activities provided by the Model Guild will be available for a $3 fee. Even dogs can have fun, with retriever demonstrations taking place along the Museum’s waterfront, and don’t miss the scenic river cruises and on-the-water oyster tonging demonstrations with Chesapeake watermen.

Conservation groups including Tilghman Islanders Grow Oysters, Chesapeake Bay Foundation, Oyster Recovery Partnership, and The Nature Conservancy will be on-hand to discuss efforts to clean and preserve the Bay. In addition, Phillips Wharf Environmental Center’s Fishmobile will offer visitors the opportunity to see live sturgeon, diamondback terrapins, horseshoe crabs, and other Bay creatures.

The event is generously sponsored by Maryland Public Television (MPT) with two MPT documentaries screened in the Van Lennep Auditorium during the event. Festival-goers can explore the CBMM’s exhibit buildings, including Oystering on the Chesapeake and Waterman’s Wharf, where visitors can try their hand at tonging or nippering for oysters. CBMM’s bugeye, Edna E. Lockwood, an 1889 log-bottomed oyster dredge boat and National Historic Landmark, will be dockside on display.

The festival takes place from 10am to 5pm on Saturday, October 28. Admission to OysterFest is free for CBMM members and children five years and under, otherwise it’s $15 for adults, $12 for seniors, and $6 for children between the ages of six and 17. Food and boat rides are an additional cost. Visit CBMM online or call 410-745-2916 for more information.

October 31—Halloween

images-4Date: Monday, October 31st for Halloween “Trick-or-Treating” for children 12 years and under from 6-8 p.m.

St. Michaels is a fun place for kids and adults to celebrate the spooky night. Residents and businesses have (almost) as much fun as the kids.

Be safe!

November 18, 10:30 a.m.—Thanksgiving Parade of Classic Cars

Screen Shot 2016-10-24 at 11.23.03 AMThe Classic Motor Museum is hosting the Third Annual Thanksgiving Parade of Classic Cars on Sat., Nov. 18. Beginning at 9 a.m. cars will line up at the Perry Cabin Ball Fields. At 10:30 the parade will proceed down Talbot St. and finish at E. Marengo St. at the Classic Motor Museum where refreshments will be enjoyed. Registration is required, and the deadline is Nov. 16. E-mail or call 410-745-8979. Donations are appreciated as we continue to raise funds to have the Education Barn doors open by the spring.

Visit the Classic Motor Museum website for more information.

A 1929 Model A Roadster leads the was among the favorites at the Classic Motor Museum parade in St. Michaels on Saturday. (Photo – Courtesy of The Star Democratic/APG Media of Chesapeake LLC)

December 2—Midnight Madness Shopping

_DSC8139View our lovely Christmas Video here!

Date: Saturday, December 2, 2017
Location: Talbot Street and throughout the town shopping area

Mark your calendar for the BIGGEST shopping day of the year! If you’ve ever been to Midnight Madness in St. Michaels, you’ll definitely be back for this year’s 14th annual event.

Great shops will be open ’til Midnight with refreshments and snacks, and special sales for that day and evening. The Town will be festively decorated for the season, and Carolers stroll the streets. You may even meet Santa…

Each year, the town of St Michaels is transformed into a picture perfect holiday postcard, the shops, restaurants and B&B’s are decorated with stunning greenery, lights and festive cheer. The holiday spirit is felt throughout town, which makes coming to St Michaels during the holiday season a special experience, year after year, and provides a wonderful backdrop to shop for the holidays.

Midnight Madness is a reminder of how important the small-business sector is to our economy and why it’s so important to “Shop Local” all year round. The movement to “Shop Local”, especially during the holidays, is needed to help support the locally owned small businesses that create jobs, boost the economy and preserve our hometown businesses.

Best of all, with every purchase you’ll receive raffle tickets to WIN fabulous prizes! Last year lucky ticket holders won over $19,000 in gift baskets, St. Michaels Shopping Dollars, and special bonus prizes.

Drawings start at 11:30 p.m. and you must present to win.

Participating restaurants and accommodations will be giving out special Ticket Redemption Coupons on December 1st and 2nd, so make your reservations today!

The drawings will be held on the deck of Marcoritaville Restaurant, on the corner of Talbot and Mill Streets on Saturday, December 5th at 11:30 p.m. and remember, you must be there to WIN! For more info, visit Midnight Madness.

December 8-10—Christmas in St. Michaels

Golden_2013 Parade 9View our lovely Christmas Video here!

Dates: December 8-10, 2017
Locations throughout the town

Friday, Gala at Harbourtowne

Saturday, Breakfast with Santa, Mid-Shore Band (Railroad), Celebration of Choirs UUMC, Parade, Santa Wonderland

Sunday, Talbot Street parade, Tour of Homes all weekend

Christmas in St. Michaels is held annually the second weekend in December in historic St. Michaels, Maryland. For more than a quarter century, both ticketed and free events including the Tour of Homes, Holiday Gala, Breakfast with Santa and largest Holiday Parade on the Eastern Shore have celebrated the arrival of the Christmas season. Proceeds from ticketed events and the sales of our very popular Collectors Ornaments have raised more than one million dollars to directly benefit local non-profit organizations in our community. We invite you to join with us as we welcome Santa, the Christmas spirit and the joy of giving.

For more information, visit

December 9 & 10—Christmas Train Village

IMG_1492Date: Friday & Saturday, December 9 & 10, 10 a.m. to 3 p.m.
Location: St. Michaels Community Center

Join our community for a Christmas Train Village Display, Gift Sale and Holiday Baked Goods Packages. No charge to see the trains. Donations accepted. Bring the whole family!