14 Things to Do in Middleburg This Weekend

— Check out our picks for Feb. 8-10, including Jazz in the Hills at 50 West, bingo at the Middleburg Community Center, a special Valentine’s tasting at Boxwood Estate Winery, and more.

Wakefield School Talent Show: Feb. 8 | 6-9 p.m.

It’s time to buy your tickets to the annual All-School Talent Show. Please join us for a fun-filled evening with talent from all three divisions as well as parents and faculty! As is tradition, the 11th grade and their advisors will be hosting the event as a fundraiser for the JR/SR Prom.


Jazz in the Hills at 50 West: Feb. 9 | 1:30-4:30 p.m.

Beat the winter blues and join 50 West for Jazz in the Hills. Enjoy music by Mangione & Benton Jazz, a guitar and piano/guitar duo featuring instrumental jazz standards from the great American standard songbook in the style of such jazz greats as Wes Montgomery, Joe Pass, Miles Davis, Duke Ellington and Dave Brubeck, also performing jazzy arrangements of popular modern songs. During Jazz in the Hills, 50 West will feature soups and delicious bread and cheese baskets paired with their wines.


Spay-ghetti & No Balls Dinner at Barrel Oak Winery: Feb. 9 | 6-9 p.m.

The Middleburg Humane Foundation wants to extend Valentine’s Day love with YOU, and what could be better than a Spay-ghetti dinner and music? Proceeds from this fun Italian dinner and raffle will support the MHF Community Cats Trap/Neuter/Return program and their low-cost spay-neuter program for low-income families. Order your tickets now — they sold out quickly last year!


Middleburg Community Center BINGO Night: Feb. 9 | 6:30-9:30 p.m.

Come to the Middleburg Community Center for an annual favorite, BINGO night! Tickets are $35 and include bingo cards, chili dinner, raffle ticket, and drink ticket. Additional drink tickets, bingo cards and 50/50 raffle tickets will also be available for purchase. Prizes will be awarded to Bingo winners! This event sells out every year, so be sure to get your tickets now. RSVP by Feb. 6 to olivia@middleburgcommunitycenter.com or call 540-687-6373.

Also this weekend

Upcoming events

Baba Jamal Koram: The StoryMan at Middleburg Library: Feb. 13 | 11 a.m.-noon

Gather around as master storyteller Baba Jamal Koram brings life to the lore of African cultures. His captivating presence engages the audience with lessons of standing up for what is right, caring for our earth, and believing in the good in everyone. For all ages.


Valentine’s Day Dinner at Harrimans Virginia Piedmont Grill: Feb. 14-16 | 5-10 p.m.

Make this romantic holiday unforgettable and treat your Valentine to an elegant dinner at Harrimans. Gaze upon sweeping views of the Virginia countryside while indulging in an enchanting five-course dinner created by Executive Chef Ryan Arensdorf. After dinner, indulge in a custom confection for two created by Executive Pastry Chef Jason Reaves.


Valentine’s Dinner at The Red Fox: Feb. 14 | 5:30-9:30 p.m.

Celebrate love at The Red Fox by treating your sweetheart to a five-course game and seafood dinner this Valentine’s Day! $175 per person, including sparkling toast. Adults only. The menu includes oysters on the half shell, lobster bisque, a duet of game, and cranberry and dark chocolate bread pudding.


Valentine’s Day Celebration at Girasole: Feb. 14 & 15 | 5-10 p.m.

Treat your Valentine to a delicious four-course meal prepared by Chef Patierno and enjoy the romantic ambiance of our dining room created by Lydia Patierno. The cost of the four-course dinner is $85 per person or $120 per person with 3 wine pairings; exclusive of tax and gratuity. The menu options include local oysters Florentine, Taleggio ravioli with aged balsamic, housemade lasagna Bolognese, housemade pastries, and more.

Also upcoming

 Remember to check our calendar for even more upcoming events!