ST MICHAELS
Flag Day 2026 Events
Clean Up + Dress Up the Town
Saturday, June 6
8:00 AM – 12:00 PM
Meet at the St. Michaels Library Parking Lot
We will kick off the celebration with a community-wide effort to clean up and decorate our town. Residents and businesses are invited to participate in beautification projects and help create a festive atmosphere throughout St. Michaels.
We kindly encourage everyone to decorate using classic red, white, and blue American décor, helping create a cohesive and timeless look throughout town.
The town has sourced its flags and bunting from:
https://www.united-states-flag.com
In coordination with St. Michaels Parks and Recreation, the St. Michaels Business Association is sponsoring a contest for the best decorated business in town. From June 6th through July 4th residents and visitors can vote for their favorite business displays via a QR code located in participating businesses. Once your vote is cast you will be entered into the drawing on July 5th to win a gift basket filled with items from your hometown shops.
Vote for your favorite patriotic decorations & enter to win a gift basket.
To volunteer, please email stmflagday@gmail.com. We look forward to seeing you there!
Concert in the Park: Special Edition
Thursday, June 11 6:00 – 7:30 PM
Muskrat Park
Experience a wonderful evening of music, community, and patriotic spirit at Muskrat Park! This special edition of our popular summer concert series blends a festive, family-friendly atmosphere with a meaningful celebration of America250.
Presented by: St. Michaels Community Center & the Parks & Recreation Advisory Board
Highlights:
Live Music: A premier performance by the United States Naval Academy Band Electric Brigade
We are beyond excited to welcome the Naval Academy Band to St. Michaels for this special event.
Parks & Poles
Historical Walking Tour
Saturday, June 13 10:00am – 3:00pm
Begins at St. Mary’s Square
Explore St. Michaels through a self guided 13 stop historical tour inspired by the number original colonies. The stops highlight our rich local history. Along the way, enjoy our beautiful parks and hear about the significance of Flag Day
Participating parks include Muskrat Park, Hollis Park, Frederick Douglass Park, Bradley Park, Back Creek Park, St. Michaels Nature Trail, and St. Mary’s Square.
The tour will be available year-round, but June 13 will feature enhanced programming.
Event Highlights:
Self-guided walking route through parks, trails, and historic areas
Multiple interpretive stations featuring:
Local and Maryland history
Stories tied to St. Michaels’ heritage
Educational information about the American flag and Flag Day
St. Michaels Art League / Plein Air Painters
Designed for individuals, families, and groups to explore at their own pace
Special Stop:
Be sure to visit the St. Michaels Talbot County Library on June 13, 10:00am – 3:00pm to experience Talbot County Celebrates the Declaration of Independence, featuring an augmented reality greeting by George Washington and Thomas Jefferson.
Make sure to stop by the Classic Motor Museum at 906 S. Talbot Street for their Flag Day Open House on June 13th from 10:00am - 3:00pm. The event will include Classic Cars, Live music, and refreshments.
For details visit: classicmotormuseum.org
Organized in collaboration with St. Michaels Parks & Rec., St. Michaels Museum, MidShore Constitution Alliance, Classic Motor Museum of St. Michaels, and St. Michaels High School.
Flag Day Picnic + Boat Parade
Sunday, June 14
10:00am – 5:00pm
Chesapeake Bay Maritime Museum
Celebrate Flag Day with a FREE, family-friendly community event featuring a full day of activities, entertainment, and waterfront fun.
We are especially pleased to welcome special musical guests:
U.S. Army Reserve 78th Army Band (Fort Dix, NJ) – their 9x9 Ensemble will be performing at the gazebo throughout the day.
Activities Include:
Classic Cars
St. Michaels Art League / Plein Air Painters
Chesapeake Independent Blues Reenactors
YMCA Field Day Games 10 - 2pm and 2 - 4pm
Boat Parade 1 - 2pm
🍷Bring your own food - beverages - chairs - blankets and enjoy a relaxing picnic on the beautiful museum grounds.
St. Michaerls 250 Boat Parade Participation:
To join the parade, please complete the registration form and return to dglackin48@gmail.com.
Form + Info
Celebrate both America’s 250th Anniversary and the St. Michaels Miles River Boat Parade.