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. JULY
Maryland Folk Festival, September 19-21, Salisbury 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 Country Calling, October 3-5, Ocean City Boardwalk First Sunday Arts Festival, October 5, Annapolis Annapolis Sailboat Show, October 9-12, City Dock, Annapolis Party in the ‘Port, October 11, Eastport Yacht Club, Annapolis Reenactment of the Burning of the Peggy Stewart, October 19, Severn River, Annapolis Maryland Avenue Fall Festival, October 19, Maryland Avenue, Annapolis Halloween Happening, *October, Anne Arundel County Fairgrounds, Crownsville SPCA Forest of Fear, *October, SPCA of Anne Arundel County, Annapolis Harvest Bash, *October, Providence Greenhouses & Gardens, Arnold Fall Fest, *October, Annapolis Town Center, Annapolis Sunfest, October 23-26, Ocean City Maryland Crab Cake Festival, October 25, Carroll County Farm Museum OysterFest, October 25, Chesapeake Bay Maritime Museum, St. Michaels NOVEMBER Annapolis Town Center Annual Christmas Tree Lighting , *November, Annapolis Lights on the Bay, *November, Sandy Point State Park, Annapolis
Eastport vs Annapolis Tug of War, *November, Spa Creek Bridge, Annapolis Fish for a Cure, November 1, Safe Harbor, Annapolis First Sunday Arts Festival, November 2, Annapolis Bay Bridge Run, November 9, Chesapeake Bay Bridge Waterfowl Festival, November 14-16, Easton Garden of Lights, *November, Brookside Gardens, Wheaton The 648 Train Garden, *November, Ferndale Volunteer Fire Company, Glen Burnie Himmel’s Holiday Village, *November, Himmel’s Landscape and Garden Center, Pasadena Grand Illumination, *November, Annapolis Lights & Leashes, *November, Sandy Point State Park, Annapolis Holiday Train Garden, November 23, Marley Station Hall North Pole Lights Walk, *November, Willow Oak Flower & Herb Farm 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 Garden of Lights, *December, Brookside Gardens, Wheaton The 648 Train Garden, *December, Ferndale Volunteer Fire Company, Glen Burnie New Year's Eve Fireworks, December 31, Annapolis Midnight Madness in Downtown Annapolis , December 4, 11, & 18, 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.
Anchors Aweigh Music Tour, July-August, United States Naval Academy, Annapolis Annapolis 4th of July Festival and Parade, July 4, Annapolis Naturalization Ceremony, July 4, William Paca House & Garden, Annapolis First Sunday Arts Festival, July 6, Annapolis Earleigh Heights Carnival, July 10-19, Earleigh Heights Fire Department, Severna Park Plein Air Easton, July 11-20, Easton Cherry Tree Young Writers’ Conference, July 15-18, Washington College, Chestertown AUGUST Annapolis Rotary Crab Feast, August 1, Navy-Marine Corps Memorial Stadium, Annapolis Casey Cares 5K Run/One-Mile Walk, August 2, Maryland Zoo, Baltimore First Sunday Arts Festival, August 3, Annapolis Made in Maryland Festival, August 10, Kurtz’s Beach, Pasadena Maryland Renaissance Festival, August 23, 24, 30, 31, Crownsville Puppy Plunge, August 24, YMCA Camp Letts, Edgewater SEPTEMBER Maryland Corn Maze, September 13-November 2, 389 Gambrills Road, Gambrills Annapolis Songwriters Festival, *September, Annapolis Kunta Kinte Heritage Festival, *September, Annapolis Maryland Renaissance Festival, September 1, 6, 7, 13, 14, 20, 21, Crownsville End of Summer Fest, September 7, Kurtz’s Beach, Pasadena First Sunday Arts Festival, September 7, Annapolis Annapolis Songwriters Festival, September 11-14, Annapolis (various locations) Annapolis Run for the Light House, September 14, Quiet Waters Park, Annapolis Bay Bridge Paddle, September 14, Annapolis
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