Great Annapolis Pumpkins, Maryland Avenue Fall Festival, and Annapolis Pride Parade make for a big weekend in Annapolis
ANNAPOLIS, MD – This weekend, Annapolis will be bursting with autumn energy as Visit Annapolis & Anne Arundel County (VAAAC) hosts Fall Family Fun Day on Sunday, October 19, from 10 a.m. to 2 p.m. at the Visitors Center, located at 26 West Street. The event promises a festive celebration for all ages, featuring face painting, hands-on crafts, and expert guidance from volunteer specialists to help guests plan their perfect fall adventure. Dogs are welcome to join in on the fun.
The fun doesn’t stop there. Just steps away, the Maryland Avenue Fall Festival offers a charming blend of seasonal celebration and local flair in one of Annapolis’s most picturesque neighborhoods. Visitors can stroll the historic avenue while enjoying live music, artisan vendors, family-friendly activities, and festive décor that captures the spirit of autumn. With cozy cafés, boutique shops, and vibrant community energy, the festival is a perfect complement to nearby events.
Adding to the excitement, Visit Annapolis & Anne Arundel County, in partnership with the Downtown Annapolis Partnership, proudly presents the Great Annapolis Pumpkins. These colossal gourds, some tipping the scales at over 1,000 pounds, are currently on display throughout the city’s historic streets, adding a whimsical touch and irresistible photo ops to the fall landscape. On October 24 (weather permitting), local and regional artists will transform these giants into stunning jack-o’-lanterns, each carved in a unique style while crowds gather to watch the magic unfold. Among the featured artists is renowned food sculptor and local teacher, Nancy Baker, whose work has been showcased on Food Channel’s Halloween Wars and commissioned by Disney Marvel, SeaWorld, and the National Zoo. To help visitors find each pumpkin, the Visitors Center will provide maps and directions, with updated locations also available at VisitAnnapolis.org.
The weekend’s festivities shine even brighter with the Annapolis Pride Parade and Festival on Saturday, October 18 with a joyful and inclusive celebration of love, identity, and community spirit. Keep an eye out for the Visit Annapolis & Anne Arundel County team, proudly marching in their signature pride shirts and sharing sweet treats along the parade route. The parade will wind through downtown, culminating in a lively festival at Maryland Hall and the Wiley Bates Athletic Complex, complete with music, food, artisan vendors, and community resources. This year’s theme, “Growing in Pride, Growing in Community,” honors the strength and unity of the LGBTQIA+ community during LGBTQIA+ History Month. For those looking to make the most of the day, swing by the Visitors Center at 26 West Street between 10 a.m. and 2 p.m., where friendly staff will be on hand to help map out a full lineup of events and discover all the vibrant happenings around town.
With a packed calendar of events, Annapolis is the place to be this weekend for families, visitors, and locals alike to enjoy the beautiful autumn weather. From pumpkins to parades, crafts to community, fall in Annapolis is a celebration visitors and residents won’t want to miss.
For details on all events happening in Annapolis and Anne Arundel County as well as visitor information, go to VisitAnnapolis.org.
About Visit Annapolis & Anne Arundel County
Visit Annapolis & Anne Arundel County (VAAAC) is a nonprofit, partnership-focused destination marketing and management organization dedicated to fostering a welcoming destination and promoting tourism for visitors, partners, and the community. The tourism and hospitality industry in Annapolis and Anne Arundel County significantly impacts Maryland's economy. In 2024, visitor spending injected $4.3 billion into the state economy, attracting more than 7.2 million visitors, and sustaining more than 27,000 jobs (both directly and indirectly), according to the 2024 Economic Impact of Tourism in Maryland Report. For more information, please visit www.VAAAC.org.
