April 5-6 (Sat/Sun)

The 2025 Art Blooms Festival is held in partnership with the National Cherry Blossom Festival, will be held at Mosaic District on

In addition to the FRESHFARM producers/farmers market vendors, there will be a stage with live music and performances, 50 craft vendors from URBN market, and children's activities on both days.

May 18 (Sun) 4:30-6:30pm

Concerts in the Park will be held at Rose Park Baseball Field. Weather permitting.

September 18-19 (Sat/Sun)

The Georgetown Fall Market, emerged from the widely successful Georgetown French Market, hosted by the Georgetown Business Improvement District every April. If you know and love the French Market, expect a similar format from this event, only with a bit of pumpkin spice. 

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Join us in Book Hill and all along Wisconsin Avenue from N Street to Reservoir Road, for small business promotions, fall-inspired menus, and autumnal activities for all to enjoy. 

September 20 (Sat) 11-7pm

Festivities will take place on South Madison St. and Federal St., which will be closed to vehicular traffic. Enjoy biergartens, traditional German food, live music and festival games. Local beer, wine, cider, and traditional Oktoberfest foods will be available for purchase from local vendors. We are also excited to bring back Artist's Alley. Coordinated by the Middleburg Arts Council, artwork from local and regional artists will be available for purchase. Regional artisans will also be present throughout the day with exhibits of fine art, pottery, jewelry, wearable art and more.

October 5, 2025 (Sun)

The popular Takoma Park Street Festival returns for its 44th year of music, vendors, food and fun in Takoma Park. This year’s festival takes place on Sunday, October 5, 2025 from 10:00 am-5:00 pm on Carroll Avenue in Takoma Park, MD to Carroll Street, NW in Takoma, DC. Festival goers will enjoy the day exploring over 185 vendor booths, live music from 18 local bands, food trucks and more. Takoma’s unique shops, restaurants and cafes are all open and welcoming visitors. Event is rain or shine.

December 5 (Sat)

8am Breakfast with Santa Middleburg Charter School

10-6pm Emmanuel Episcopal Church 77th Annual Christmas Shop

11am Middleburg Hunt Review

2pm Community Christmas Parade

Join in one of the most fun-filled family festivals of the year in Middleburg with activities, special events, great eats, the famous Middleburg Hunt Review and a mile-long Christmas parade. Afterwards, experience a Middleburg evening in our bistros, cafes, pubs, and restaurants joining in the Spirits of Middleburg.

The town of Middleburg, VA has been featured in several national publications starting with Southern Living (October 2024), Wine and Country(Holiday Edition), Country Living(November 2024) and Vogue Magazine(December 2024) as “One of the best Christmas Towns in the USA”.

Please watch this page as we continue to add festivals and events to our 2025 calendar. Thank you!