Calvert County will kick off the holiday season with its annual A Main Street Christmas celebration, featuring a tree lighting on December 5, 2025, and a parade plus historical open house on December 13, 2025, all centered in downtown Prince Frederick.
The free events draw families to the county seat for live music, Santa visits, a parade, and seasonal activities organized by multiple county departments and community partners. Calvert County Parks & Recreation leads coordination alongside the departments of Economic Development, Public Works, Communications & Media Relations, the Sheriff’s Office, the Calvert County Historical Society, Calvert Garden Club, and Arts Council of Calvert County.
The series opens Friday, December 5, from 4:30 p.m. to 6:30 p.m. on the Calvert County Courthouse lawn at 175 Main Street. Activities start at 4:30 p.m. with arts and crafts, live performances, and photos with Santa. The tree lighting ceremony begins at 5 p.m., featuring a large evergreen decorated by the Calvert Garden Club with traditional greenery and lights that remain illuminated through the season on the historic courthouse grounds.
One week later, Saturday, December 13, brings the Calvert County Holiday Parade from 10 a.m. to noon. Hosted by Parks & Recreation, the route starts near the intersection of Church and Main streets, proceeds south on Main Street, turns onto Dares Beach Road briefly before entering Duke Street, loops through the Prince Frederick Shopping Center, and returns along Church Street. Marching bands, floats, emergency vehicles, and community groups participate annually.
Immediately after the parade, from noon to 4 p.m., the Calvert County Historical Society opens Linden, the 1840s Federal-style mansion at 70 Church Street, for an old-fashioned Christmas. Visitors tour rooms decorated in period style with fresh greens, vintage ornaments, and historical displays reflecting 19th- and early 20th-century holiday traditions in Southern Maryland. The event includes docent-led insights into how Calvert families once celebrated the season at the home that served as county headquarters during the Civil War era.
Free public parking supports both December 13 events at the District Courthouse lot on Duke Street, the Circuit Courthouse lower lot on Main Street, King Memorial Park on Duke Street, the lot at 15 Duke Street, and designated spaces at the Sheriff’s Office on Church Street for accessible needs. A detailed map appears on the county’s special events page at CalvertCountymd.gov/SpecialEvents.
Community groups and organizations can still enter the parade by submitting forms before the December 1, 2025, deadline at 5 p.m. Entries range from scout troops and church groups to dance teams and classic cars, with judging categories for best float, marching unit, and holiday spirit.
The tradition traces back more than two decades as a way to highlight Prince Frederick’s walkable downtown during the holidays and support local commerce. Main Street becomes partially closed for the parade, allowing safe viewing from sidewalks lined with shops and restaurants that often extend hours or offer specials.
Weather contingencies follow standard county protocols; updates post to the special events page or the county’s social media channels if rain or wind forces adjustments, though the tree lighting and Linden open house proceed indoors or under cover as needed.
Residents familiar with the courthouse square recognize it as the same lawn used for summer concerts and the county fair’s administrative hub, now transformed each December into the community’s central gathering spot. Linden, listed on the National Register of Historic Places, regularly opens for tours but reserves this date for full holiday immersion, complete with wassail and period music.
Full schedules, registration forms, route maps, and contact information remain available online at CalvertCountymd.gov/SpecialEvents or by calling Parks & Recreation at 410-535-1600, extension 2649.