By Cayla Gardner
Fall is one of the best times to explore all that Montgomery County has to offer. With events happening most weekends, your schedule will be jam-packed. Choose between family-friendly festivals, Halloween movies, live performances and seasonal markets.
Here’s a look at some of the top events taking place throughout October and November.
Key takeaways
- The bigger picture: Halloween celebrations begin early with a pumpkin race and last until the end of October with a Fall-O-Ween celebration.
- The details: Catch live performances, ranging from concerts and plays to comedy and magic shows, throughout the fall.
- The more you know: The cool weather brings tasty treats with the DMV Chocolate and Coffee Festival happening the second weekend of November.
October 2026
Shady Grove Farmers Market
Open every Wednesday throughout the month of October, customers can purchase fresh fruit, veggies, baked goods, arts, jewelry and more. The market is located Rockville and runs from 11 a.m.-2 p.m.
Oct. 3 & 31, 2026
The Magic Duel Comedy Show
Audience participation takes center stage during “The Magic Duel,” a high-stakes interactive show where two magicians compete for the crowd’s votes. Hosted by Mark Phillips and Meadow Perry, the 90-minute performance gives viewers mind-bending illusions, hilarious jokes and an experience to remember.
Oct. 3, 2026
The Great Pumpkin Race and Fall Festival
Watch handcrafted pumpkin race cars speed down the track during The Great Pumpkin Race, a side-by-side, single elimination competition. Participants come together for a chance to compete for the Pumpkin Race Championship Trophy in the final event of the North Creek Community Center Fall Festival.
Oct. 9, 2026
Halloween Outdoor Movie Night
Bring the whole family together for a family-friendly outdoor screening of “Hocus Pocus” at Twinbrook Quarter Central Park. Bring your blankets and lawn chairs for an evening under the stars, complete with free popcorn, Halloween sweets, face painting and more.
Oct. 18, 2026
Chucho Valdés 85th Birthday Celebration
Celebrate legendary pianist Chucho Valdés as he commemorates his 85th birthday with a special performance at the Music Center at Strathmore. Best known as the founder of the influential band Irakere, Valdés helped revolutionize Latin jazz and has earned seven Grammy Awards and seven Latin Grammy Awards.
Oct. 25, 2026
Silver Spring Fall-O-Ween
Located at Veterans Plaza, this festive fall celebration is the perfect way to spend your Saturday afternoon. Packed with costume parades, arts and crafts vendors and plenty of Halloween treats, this family-friendly event is an easy way to celebrate the season.
Oct. 26, 2026
An Evening of Alton Brown
Join television personality and James Beard Award winner Alton Brown for an evening of his signature blend of food, science, comedy and music. Fans of his shows “Good Eats,” “Iron Chef America” and “Cutthroat Kitchen” can expect demonstrations, storytelling and plenty of laughs.
Oct. 31-Nov. 15, 2026
Rockville Musical Theatre Presents: “Caroline, Or Change”
Rockville Musical Theatre presents the Tony-nominated musical “Caroline, Or Change” at the F. Scott Fitzgerald Theatre. Set during 1963, the play follows the Gellman family and their African-American maid, Caroline, as they navigate one of the most pivotal periods in American history. Featuring a score that blends blues, gospel and traditional Jewish melodies, this powerful and passionate production will be performed eight times during its run.
Nov. 7-8, 2026
DMV Chocolate and Coffee Festival
Sweeten your senses and sip coffees from around the world while browsing unique vendors offering teas, soaps, candles, gifts and art at the DMV Chocolate and Coffee Festival. Families can also enjoy classes and presentations, coffee demonstrations and a kids’ coffee filter craft table.
Nov. 18, 2026
Grand Kyiv Ballet Presents “The Swan Lake: Symphony of Lights”
Experience a fresh interpretation of the classic ballet as the Grand Kyiv Ballet presents “Swan Lake: Symphony of Lights.” This production, which reimagines the iconic Tchaikovsky ballet, brings together vivid light design, illuminated costumes and elite dancers.
