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 12 months. Some dates have not been set but are typically during the month as listed.
Drink Maryland, Centreville, June Paint Annapolis, Annapolis, June 1-8 Santa Maria Cup, Annapolis, June 2-7 Let's Go! Music Festival, Annapolis, June 6-7 Giant Annual Barbecue Battle, Washington, DC, June Annapolis Arts Month, Annapolis, June Annapolis Juneteenth Parade & Festival, Annapolis, June 21* Bands in the Sand, Annapolis, June 14 Cape St. Claire Strawberry Festival, Annapolis, June DMV R&B Neo Soul Wine Festival, Crownsville, June Naptown Challenge, Annapolis, June 30 - July 2 JULY Annapolis 4th of July Festival and Parade, Annapolis, July 4 First Sunday Arts Festival, Annapolis, July 6 Plein Air Easton, Easton, July 11-20 Illuminate Annapolis Mind-Body-Spirit- Arts Festival, Arnold, July AUGUST Annapolis Rotary Club Crab Feast, Annapolis, August 1 Baltimore Artscape, Baltimore, August First Sunday Arts Festival, Annapolis, August 3 Maryland Renaissance Festival, Crownsville, August 23 - October 19 SEPTEMBER First Sunday Arts Festival, Annapolis, September 7 Anne Arundel County Fair, Crownsville, September Annapolis Songwriters Festival, Annapolis, September Maryland Seafood Festival, Annapolis, September Maryland Folk Festival, Salisbury, September 19-21 Annapolis Baygrass Music Festival, Annapolis, September 20-21
West Annapolis Oktoberfest, Annapolis, September Oceans Calling Festival, Ocean City, September Bohemian Black Festival, Severna Park, September Annapolis Italian Festival, Annapolis, September Kunta Kinte Heritage Festival, Annapolis, September Wine On The Beach, Ocean City, September 5-6 OCTOBER Art @ the Park, Annapolis, October International Edgar Allan Poe Festival & Awards, Baltimore, October* Sunfest, Ocean City, October* Annapolis Powerboat Show, Annapolis October 2-5 Annapolis Sailboat Show, City Dock, Annapolis, October 9-13 NOVEMBER Annapolis Town Center Annual Christmas Tree Lighting, Annapolis, November* Lights on the Bay, Annapolis, November 2025 - January 1, 2026 DECEMBER Menorah Lighting at Annapolis Town Center, Annapolis, December Midnight Madness in Downtown Annapolis, Thursdays in December Annapolis Chocolate Binge Festival, December 7 Eastport Yacht Club Lights Parade, Annapolis, December 13, New Year's Eve Fireworks, Annapolis, December 31
FEBRUARY Chesapeake Fire & Ice Festival, Easton, February 16 - 17 Annapolis Restaurant Week, Annapolis, February 24 - March 3 MARCH "St. Patrick’s Hooley, St. Patrick's Day Parade, Annapolis March 8 and 9 Maryland Day Celebration, Anne Arundel County, March 21 - 23 Annapolis Running Festival, Annapolis, March 22 APRIL Anne Arundel Asian American Festival, Crownsville, April Annapolis Film Festival, Annapolis, April Bay Bridge Boat Show, Stevensville, April 11 - 13 Eastern Shore Sea Glass & Coastal Arts Festival, St. Michaels, April 12 - 13 Maryland Chicken Wing Festival, Crownsville, April Springfest, Ocean City, April 24-27 Annapolis Spring Sailboat Show, Annapolis, April 25 - 27 MAY Annapolis Book Festival, Annapolis, May 3 Annapolis Irish Festival, Crownsville, May 2-3 Fairy House Festival, Annapolis, May First Sunday Arts Festivals, Annapolis, May 4 Let’s Go! Music Festival, Crownsville, May - June May Day in Annapolis, Annapolis, May 1 May Day Faerie Festival, Essex, May Naptown Music Feast, Crownsville, May Santa Maria Cup, Annapolis, May U.S. Naval Academy Commissioning Week, Annapolis, May 16-23* Oxford Fine Arts Fair, Oxford, May 16-18 Annapolis Pride Parade & Festival, Annapolis, May 31 JUNE Annapolis Greek Festival, Annapolis, June
*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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