2025 Festivals & Events The Annapolis area has an abundance of festivals and celebrations for the whole family! Some are a little further out of Annapolis, but are worth the drive. Here are all of the best fests to plan your schedule for the next several months. Some dates have not been set but are typically during the month as listed.
Annapolis Baygrass Music Festival, September 20-21, Sandy Point State Park, Annapolis Oceans Calling Music Festival, September 26-28, Ocean City West Annapolis Oktoberfest, September 28, Annapolis Wine On The Beach, September 5-6, Ocean City OCTOBER International Edgar Allan Poe Festival & Awards, *October, Baltimore Art @ the Park, *October, Annapolis Annapolis Powerboat Show, October 2-5, City Dock, Annapolis First Sunday Arts Festival, October 5, Annapolis Annapolis Sailboat Show, October 9-12, City Dock, Annapolis Sunfest, October 23-26, Ocean City NOVEMBER Annapolis Town Center Annual Christmas Tree Lighting , *November, Annapolis Lights on the Bay, *November, Sandy Point State Park, Annapolis First Sunday Arts Festival, November 2, Annapolis Waterfowl Festival, November 14-16, Easton Grand Illumination, November 30, Annapolis DECEMBER Lights on the Bay, *December, Sandy Point State Park, Annapolis Menorah Lighting at Annapolis Town Center, *December, Annapolis Annapolis Chocolate Binge Festival, December 7, Annapolis Eastport Yacht Club Lights Parade, December, Annapolis New Year's Eve Fireworks, December 31, Annapolis Midnight Madness in Downtown Annapolis , December 4, 11, & 18, Annapolis
Paint Annapolis, June 1-8, Annapolis National Music Festival, June 1-14, Chestertown Santa Maria Cup, June 2-7, Annapolis Let's Go! Music Festival, June 6-7, Anne Arundel County Fairgrounds, Crownsville Cape St. Claire Strawberry Festival, June 7, Annapolis Antique & Classic Boat Festival and Coastal Arts Fair, June 13, St. Michaels Bands in the Sand, June 14, Chesapeake Bay Foundation, Annapolis DMV R&B Neo Soul Wine Festival, June 14, Brandywine 2025 Air Dot Show Tour, June 14-15, Ocean City Annapolis Juneteenth Parade and Festival, June 21-22, Downtown Annapolis & Anne Arundel County Fairgrounds, Crownsville JULY Annapolis 4th of July Festival and Parade, July 4, Annapolis First Sunday Arts Festival, July 6, Annapolis Plein Air Easton, July 11-20, Easton AUGUST Annapolis Rotary Crab Feast, August 1, Navy-Marine Corps Memorial Stadium, Annapolis First Sunday Arts Festival, August 3, Annapolis Maryland Renaissance Festival, August 23, 24, 30, 31, Crownsville SEPTEMBER Annapolis Songwriters Festival, *September, Annapolis Kunta Kinte Heritage Festival, *September, Annapolis Maryland Renaissance Festival, September 1, 6, 7, 13, 14, 20, 21, Crownsville First Sunday Arts Festival, September 7, Annapolis Bay Bridge Paddle, September 14, Annapolis Maryland Folk Festival, September 19-21, Salisbury
APRIL West Annapolis Spring Festival, April 4, Annapolis Annapolis Cup Croquet Match, April 5, St. Johns College, Annapolis Maryland Chicken Wing Festival, April 5, Anne Arundel County Fairgrounds, Crownsville Anne Arundel Asian American Festival, April 6, Anne Arundel County Fairgrounds, Crownsville Bay Bridge Boat Show, April 11-13, Grasonville Eastern Shore Sea Glass & Coastal Arts Festival, April 12-13, St. Michaels Lemon Fest 2025, April 26, Laurel Springfest, April 24-27, Ocean City Annapolis Spring Sailboat Show, April 25-27, City Dock, Annapolis MAY May Day, May 1, Annapolis Annapolis Irish Festival, May 2-3, Anne Arundel County Fairgrounds, Crownsville Annapolis Book Festival, May 3, Key School, Annapolis 2025 May Day Faerie Festival, May 3-4, Essex 3rd Annual Songbird Festival, May 4, Maryland Hall, Annapolis First Sunday Arts Festival, May 4, Annapolis Oxford Fine Arts Fair, May 16-18, Oxford US Naval Academy Commissioning Week, May 16-23, Annapolis U.S. Naval Academy Air Show, May 21, Annapolis Boardwalk Rock, May 17-18, Ocean City Fairy House Festival 2025, May 17-June 22, Quiet Waters Park, Annapolis Baltimore Artscape, May 24-25, Baltimore Annapolis Pride Festival and Parade, May 31, Annapolis JUNE First Sunday Arts Festival, June 1, Annapolis Annapolis Arts Month, June, Annapolis
*Specific date to be determined. All dates and times are correct at the time of publishing, but we always recommend double checking the festival websites for any changes before finalizing your plans.
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