2024-2025 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.
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 Illuminate Annapolis Mind-Body-Spirit- Arts Festival, Arnold, July Plein Air Art Festival, Easton, 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 Annapolis Baygrass Music Festival, Annapolis, September 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
OCTOBER Annapolis Powerboat Show, Annapolis, October 3 - 6 International Edgar Allan Poe Festival & Awards, Baltimore, October 4 - 6 First Sunday Arts Festival, Annapolis, October 6 USA BMX East Coast Nationals: Chesapeake BMX, Severn, October 11 - 13 Art @ the Park, Annapolis, October 12 - 13 Annapolis Sailboat Show, Annapolis, October 10 - 14 Sunfest, Ocean City, October 24 - 27 Great Annapolis Pumpkins, Annapolis, October 7 - November 3 NOVEMBER First Sunday Arts Festival, Annapolis, November 3 Waterfowl Festival, Easton, November 8 - 10 Lights on the Bay, Annapolis, November 19 - January 1 Annapolis Town Center Annual Tree Lighting Ceremony, Annapolis, November 17 Annapolis Jazz & Roots Festival, Annapolis, November 3 - 12 DECEMBER New Years Eve Fireworks, Annapolis, December 31 Annapolis Chocolate Binge Festival, Annapolis, December 1 Downtown Annapolis Grand Illumination, Annapolis, December 1 Eastport Yacht Club Lights Parade, Annapolis, December 14 Menorah Lighting at Annapolis Town Center, Annapolis, December Midnight Madness, Annapolis, December 5, 12, 19 FEBRUARY Chesapeake Fire & Ice Festival, Easton, February 16 - 17 Annapolis Restaurant Week, Annapolis, February 24 - March 3
MARCH Maryland Day Celebration, Anne Arundel County, March 21 - 23 Annapolis Running Festival, Annapolis, March Irish Hooley, Shamrock the Dock, St. Patrick’s Day Parade, Annapolis, March APRIL Anne Arundel Asian American Festival, Crownsville, April Annapolis Film Festival, Annapolis, April Annapolis Spring Sailboat Show, Annapolis, April 25 - 27 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 MAY Annapolis Book Festival, Annapolis, May 3 Annapolis Irish Festival, Crownsville, May 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 Springfest, Ocean City, May 1 - 4 U.S. Naval Academy Commisioning Week, Annapolis, May Annapolis Pride Parade & Festival, Annapolis, May 31 JUNE Annapolis Greek Festival, Annapolis, June Drink Maryland, Centreville, June Giant Annual Barbecue Battle, Washington, DC, June Annapolis Arts Month, Annapolis, June Annapolis Juneteenth Parade & 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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