Events


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Golden_2013 Parade 9View our lovely Christmas Video here!

Dates: December 11-13, 2020
Locations throughout the town

Friday, Gala at Miles River Yacht Club

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

Sunday, 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 us as we welcome Santa, the Christmas spirit and the joy of giving.

For more information, visit www.christmasinstmichaels.org

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Date: December TBD, 2020, 10 a.m. to 3 p.m.
Location: St. Michaels Community Center

Once again, SMCC plays host to the Annual Christmas Train Village Display, Gift Sale and Holiday Baked Goods, open to the public. Baked goods and crafts will be for sale on Saturday (after the parade) and Sunday. There is no charge to see the trains. Donations are gratefully accepted. Fun for all kids of all ages!!!

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St. Michaels Xf V-day 300x600Winter is a very romantic time in St. Michaels! Cozy inns, elegant and relaxed dining, wonderful shops (many with lovely jewelry, hint, hint.)
Watch a Winter Romance video here!

LIKE our Facebook page!

Visit our calendar of events page!

Plan your visit here!

Here are some of the things they are saying about us:

“My day to day life is very stressful and I don’t really have a lot of time to relax. I finally got a weekend off and my boyfriend surprised me with a romantic weekend getaway to St. Michaels. The owners were extremely nice and helpful. They gave us the best tips for our weekend and were very accommodating. We had room 1 on the first floor. It was cozy with a king size bed, very comfortable, and nice little fireplace for the evening. We did not have a tv in our room which was absolutely amazing for getting away. However, there was a tv in the lounge area with dvd’s, plenty of books to read and complimentary coffee, hot tea, cider, hot chocolate, and little pastries. Each morning we awoke to the amazing smells coming from the kitchen and warm voices for conversation. The food was incredible. Fresh ingredients all prepared each morning. I really appreciate the care they put into everything. They shared stories about the history of the town and we always had an abundance of conversation. The town was quaint and beautiful with a lot of neat little stores and excellent cuisine. Weather was great with a slight breeze from the water. We will definitely be back.”


“My choice for a weekend winter escape! No Crowds! Shopping, Cafés, Museums, Pubs & Saloons, all with no crowds! ENJOY!”

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Date: March TBD, 2021
Website: HERE

The St. Michaels ChocolateFest and will include restaurant chefs conjuring up amazing delectable special menu items to showcase chocolate inspired dishes and desserts. Our inns and bed and breakfasts will feature chocolate inspired get-away packages…chocolate spa treatment anyone? Chocolate lovers will enjoy strolling throughout the Town of St. Michaels to indulge in thousands of chocolate concoctions on Saturday, March TBD, 2021 from 11:00 a.m. – 4:00 p.m. during the Chocolate Crawl, sampling amazing artisan chocolates, desserts, locally crafted wine, beer and spirits. Pre-Purchase Chocolate Crawl Tasting Tickets (minimum 5 tickets).

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Shopping CartEvery year on March 17, the Irish and the Irish-at-heart across the globe observe St. Patrick’s Day. What began as a religious feast day for the patron Saint of Ireland has become an international festival celebrating Irish culture with parades, dancing, special foods and a whole lot of green.

St. Michaels is joining the St. Patrick’s Day celebration with special events. The annual Carpenter Street Saloon shopping cart races are held every year on St. Patrick’s Day at Midnight. Proceeds benefit the St. Michaels and Tilghman Fire Departments.

The Blackthorn Irish Pub will have their annual event with live music and Bag Pipers.

Participating businesses will have specials all weekend long.

Buy a personalized shamrock to adorn the street! $50 each to support the St. Michaels Police Department “S.M.Y.L.E” Program (St. Michaels Youth Law Enforcement) which is a great program which educates kids about law enforcement.

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Daffodil Days is cancelled due to the recent Governor’s order during this health Crisis, but please enjoy a VIRTUAL DAFFODIL DAYS TOUR video HERE 

Still want to enter the VIRTUAL Daffy-Dog Contest? Just dress your pup in a daffodil these and send us your photos HERE by April 28th.

3RD ANNUAL DAFFODIL DAYS
Join us for our fabulous floral festival! Take a self-guided Daffodil Tour. Pick up a map to tour and see the tens of thousands of Daffodils planted throughout our lovely waterfront town! Enter your house or your business window in the daffodil decorating contest. Dress up your pooch or your pooches for the Daffy-Dog Costume Contest at 11 a.m. in Muskrat Park with winners for individual and groups of pups. Take a historic walking tour at 2 p.m. the St. Michaels Museum and get free seeds at the seed library at the St. Michaels Library. See members of the St. Michaels Art League do plain air painting of the large array of daffodil beds throughout the town with art sales from 2-3 p.m. on the corner of Talbot and Railroad. Look for exciting details for the 2021 event on the DAFFODIL DAYS WEBSITE!

Want to participate? Visit the ST. MICHAELS IN BLOOM WEBSITE! St. Michaels In Bloom is a newly formed community organization dedicated to the beautification of St. Michaels. Consisting solely of volunteers, St. Michaels in Bloom works to create a welcoming and vibrant landscape for our town through the planting colorful flowers, plants, and trees throughout our business and community districts. Part of the national organization, America in Bloom, whose vision is to have localities across the US participate in community beautification projects, the goal of St. Michaels in Bloom is to see our community bloom in many ways.

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Dates: April 4&5, 2020, Saturday, 10 a.m. to 5 p.m. & Sunday 10 a.m. to 4 p.m.
Location: Chesapeake Bay Maritime Museum

INFORMATION FROM 2019 FESTIVAL BELOW…

The 8th annual Eastern Shore Sea Glass and Coastal Arts Festival in St. Michaels, Md. now has a larger, waterfront location at the Chesapeake Bay Maritime Museum. The festival takes place at CBMM on Saturday, April TBD, 2020 from 10–5 pm and Sunday, April 7, 2019 from 10–4 pm. The new venue also expands the festival—which was previously held at the Old Mill in St. Michaels—to include scenic river cruises, live music, food, and libations. The Sea Glass Festival will feature more than 70 artisans many from the local Delmarva area, and others travelling from as far away as New England—who will exhibit and sell coastal and sea-glass related jewelry, home décor, art, and more. The festival also includes educational lectures about sea glass and its history along the shores of the Chesapeake Bay.

The Sea Glass Center will be exhibiting Beach Finds of the Chesapeake in CBMM’s Van Lennep Auditorium, which explores a sampling of the different types of finds discovered by those who seek to preserve the history of our region by collecting fragments of its past. From shark teeth and other 20-million-year-old Miocene-era fossils, through Victorian doll parts and marbles, to modern plastic toys and marine debris found today, the Chesapeake Bay holds history, treasures and trash alike to be discovered by beachcombers who search its disappearing shorelines.

The Sea Glass Center is a non-profit organization preserving and presenting the historical, artistic, and cultural significance of sea glass through education. The exhibit will be on display during the festival and at CBMM through June 29, 2019.

The two-day festival ticket includes entrance to the Eastern Shore Sea Glass and Coastal Arts Festival, educational lectures and documentaries, live music, all of the exhibitions and historic structures on the campus of the Chesapeake Bay Maritime Museum and is set at $15 for adults; $12 for seniors and retired military; $6 for children 6–17; $5 for CBMM members and active military (ID required); and free for member children 6–17 and all children 5 and under. Advanced admission tickets can be purchased online at web address, with tickets also sold at CBMM the day of the event.

Boat rides, food and beverages will be available for purchase, including beer, wine, and cocktails. Additional free event parking will be available at St. Michaels High School, with a complimentary shuttle service to and from CBMM running throughout the day.

For safety reasons, non-service dogs need to be kept home during CBMM festivals, including the Eastern Shore Sea Glass and Coastal Arts Festival. Carry-on alcohol from dock or land is prohibited.

The Chesapeake Bay Maritime Museum is a non-profit educational organization dedicated to preserving and exploring the history, environment, and culture of the entire Chesapeake Bay region, and making this resource available to all. Every aspect of fulfilling this mission is driven by CBMM’s values of relevancy, authenticity, and stewardship, along with a commitment to providing engaging guest experiences and transformative educational programming, all while serving as a vital community partner. For more information, visit cbmm.org or call 410-745-2916.

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To keep up our spirits up during these tough times, Commissioner Dennis Glackin is spearheading a Town-wide fun event (thanks for the idea, Mary Lou McAlister) to have residents monitor how much they walk and turn it into a fun contest. The Governor’s Stay-at-Home Order encourages enjoying the outdoors and exercising while maintaining the 6’ social distancing.

The first week of the walking challenge has concluded.   Note: certain classes have been combined as there weren’t enough entries to keep things competitive.  The leaders as of Saturday, April 11 are as follows:

19-55 age group – Sherry, 8 hours
56-75 age group – Angeline, 12.25 hours
Over 75 – Deborah, 14 hours

Remember, I need your TIME spent walking. Time in minutes or hours is acceptable to submit. Steps don’t count. Next results due Saturday, April 18 at dglackin@stmichaelsmd.gov. Keep up the good work!

Here are the rules if you want to join in!

  • The contest starts Saturday April 4th, and ends at midnight on Thursday, April 30th.
  • Age groups are 5-18; 19-35; 36-55; 56-75; and over 75
  • Register with Dennis Glackin with your name, address and email address at dglackin@stmichaelsmd.gov and report the count of how many minutes you walk to him every Saturday. (Obviously, we will be operating on the Honor System.)
  • Stop and chat times during the walk should be excluded from the time walking, but are encouraged along the way (6 feet apart).
  • All walking should be outdoors, unless there is a physical reason that is not possible, then indoor walking can be counted.
  • When the stay-at-home order is lifted, we will have a Town-wide awards ceremony at Muskrat Park for the top finishers in each age category.
  • Check the At Home in St. Michaels Facebook page HERE for updates.
  • Remember…keep your social distancing.

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The St. Michaels in Bloom Daffodil Days events were cancelled, but you can STILL send us your photos to compete in our VIRTUAL Daffy-Dog Costume Contest! Dress your pooch in a daffodil theme! Prizes for 1st, 2nd and 3rd place will be awarded in two categories – Best Individual and Best Group. Just be creative, email us a photo of your pup(s) to stmichaelsinbloom@gmail.com by April 28th and we will post the photos on the “St. Michaels in Bloom” Facebook page and pick a winner!

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Date: Friday, VIP evening events. April TBD 2021 from Noon-5 p.m.
Locations: Throughout the town

Visit the WineFest website for information and tickets!

Join us at Maryland’s premiere wine event, featuring over 400 wines from around the globe. Now in its 11th year, WineFest is a streetscape event held throughout the town of St. Michaels. Wine tastings, great food, retail specials, and much more. Wine aficionados will experience hundreds of highly-rated U.S., international, and Maryland wines. Each wine venue will be retailing wine at special WineFest discount pricing. Some of these wines are in very limited supply and in some cases only available at Winefest!

Two VIP tasting venues will be available for tasting premium wines often not available in Maryland. One VIP venue will be on the Patriot Cruise Boat where you will taste fine wines while cruising the Miles River. The other VIP venue will be at the Old Brick Inn. At the conclusion of your two great VIP tasting experiences, all of the wines you have tasted will be available for purchase at the Old Brick Inn.

All attendees will be able to “Walk throughout St. Michaels” using a WineFest map as their guide or ride the shuttle buses provided by WineFest.