The holiday season is arriving in Culpeper Downtown, and the community is invited to celebrate with festive events, holiday shopping opportunities, family entertainment, and small-town holiday charm during Culpeper Downtown for the Season 2026, presented by Culpeper Renaissance, Inc. (CRI). The festivities will take center stage on Sunday, November 22, with the Holiday Open House & Community Tree Lighting, bringing families and visitors downtown for an afternoon of free entertainment, seasonal activities, local shopping, and holiday cheer. From carriage rides and live music to face painting, balloon art, and a special visit from the Grinch, the event offers something for all ages as downtown welcomes the holiday season. Activities will take place throughout downtown, with entertainment beginning as early as 10 a.m. and continuing into the afternoon. The community tree lighting ceremony will begin at 4:50 p.m.
Families can enjoy a variety of free entertainment throughout the day, including carriage rides departing from the Train Depot from 11 a.m. to 3 p.m., Doodling Queen Face Painting from 11 a.m. to 2 p.m., and Sandy’s Face Painting from 2 to 5 p.m. A roaming magician will entertain visitors from noon to 4 p.m., while Brennan’s Balloons will create colorful balloon designs from noon to 3 p.m. The Culpeper County High School Band will perform on the Grass Rootes porch from 1 to 3 p.m., and children can enjoy a bounce house near the LOVE sign from 10 a.m. to 5 p.m. Visitors are also encouraged to stop by the State Theater from noon to 4 p.m. for Giving Locally for the Holidays, an opportunity to meet local nonprofit organizations, learn about their missions, and discover ways to give back to the community. Participating organizations will decorate their tables for the holiday season, and families can enjoy a special photo opportunity with the Grinch. In addition to the scheduled entertainment, visitors can explore downtown shops, discover unique gifts, enjoy local restaurants, and experience the welcoming atmosphere that makes Culpeper special during the holidays.
Families will also have a special opportunity to visit with Santa during the celebration. Santa will be at the Culpeper Visitors Center from 2 to 5 p.m., where children can share their holiday wish lists, make their Christmas requests, and enjoy a free photo opportunity. Santa will then join the community to celebrate the lighting of the downtown Christmas tree, with the ceremony beginning at 4:50 p.m.
Culpeper Downtown for the Season also features several designated shopping days to encourage residents and visitors to shop locally, take advantage of in-store specials and support the independent businesses that make downtown unique. The season begins with Pink Friday on November 20. Shoppers can continue their holiday shopping on Black Friday, November 27, and Small Business Saturday, November 28, before taking advantage of Cyber Monday on November 30. Holiday Sunday Funday on December 6 will offer additional family-friendly shopping opportunities and kid-friendly specials. Participating businesses may offer their own promotions and activities, with shopping events based on individual store business hours.
The holiday celebrations continue throughout the season with additional opportunities for families to visit Santa and enjoy downtown traditions. Santa will be roaming around downtown during Small Business Saturday, November 28, from 1 to 5 p.m., and during Holiday Sunday Funday on December 6 from 2 to 5 p.m. at Angry Wife Brewhouse. The Culpeper Downtown Window Decorating Contest, taking place November 18–22, will invite the community to enjoy festive storefront displays throughout downtown. On December 6, the Culpeper Christmas Parade will bring holiday excitement to Main Street, beginning at 5 p.m. The Culpeper Downtown Winter Farmers Market will also return on December 5, 12, and 19, offering locally grown products, handmade goods, and seasonal favorites from 10 a.m. to 2pm at the new Heritage Park parking lot.
Culpeper Downtown for the Season is made possible through the generosity of sponsors, local businesses, and community partners who help bring holiday traditions and family-friendly experiences to Culpeper Downtown. Culpeper Renaissance, Inc. extends its appreciation to this year’s sponsors, including Country Chevrolet, Kid Central, Appleton Campbell, Oak View National Bank, UVA Community Credit Union, Duckett Corbin Team Realtors w/ RE/MAX Gateway, Able Heating & Air, YHB, 103.1 WJMA 95.3 SAMFM, Culpeper Times, Culpeper Media Network and the many additional businesses and organizations supporting this year’s festivities. Their contributions help create memorable experiences for residents and visitors while supporting the continued vitality of Culpeper Downtown.
Culpeper Downtown for the Season celebrates the community spirit, local businesses, and holiday traditions that make downtown a special place to gather. Whether visitors are beginning their holiday shopping, bringing their children to enjoy an afternoon of entertainment, visiting Santa, or gathering with family and friends for the community tree lighting, downtown Culpeper offers plenty of opportunities to make lasting holiday memories. For the complete schedule of events and additional information, visit www.culpeperdowntown.com and follow Culpeper Renaissance, Inc. on social media for updates throughout the holiday season.