How to Welcome Fall in DC

September 4, 2025 | Lifestyle

Whether you’ve been soaking up every last minute of summer or anxiously awaiting the start of fall, there’s no denying the magic of autumn in DC.

Starting this month, every corner of the city will be primed with colorful attraction upon colorful attraction — and we’re here to help you experience each one before the last leaf falls.

Keep reading for the most festive ways to welcome fall in style this year!

Hoping to sell your home before Winter arrives? Click here to read our blog about selling your home before the end of the year.

#1 Visit A Cidery: The DMV is teeming with quality cideries, where you can sample some seriously tasty — and let’s not forget boozy — apple juice. First up, there’s Lost Boy Cider Taproom in Alexandria. Meanwhile, those with access to a car can make the scenic voyage out to one of the many cideries in Virginia and Maryland, such as the Cider Barn at Mt. Defiance in Middleburg, or Willow Oaks Craft Cidery in Middletown, Maryland’s oldest organic farm.

#2 Celebrate Snallygaster: Those in the know will know: Snallygaster is the District’s biggest beer festival — bar none. And on October 11th, the merry monster returns to DC for its 12th year — a rollicking celebration of all things craft beer. Festival-goers can sip their way through more than 450 draft pours, casks, gravity kegs, and bottles from 175+ top American and international producers, all while enjoying bites from local food trucks and live music across two stages.

#3 Sip And Get Spooked: It wouldn’t be fall without a quintessential vineyard trip and a festive ghost tour — so why not roll them into one perfect fall activity? Luckily, this year, a frightful tour given at the Winery at Bull Run from September 28th-October 30th combines two favorite fall pastimes: drinking wine and listening to ghost stories. Instead of your typical ghost tour that would lead you through town, this one takes place at a winery, and is led by lantern through the historic grounds. Tickets include the tour, a wine tasting, a glass, and exclusive access to the winery after hours.

Looking for more ways to enjoy autumn in DC? Check out these posts below:

#4 PYOP (Pick Your Own Pumpkin): Fall just isn’t complete until you’ve purchased at least one pumpkin that you may or may not actually carve. Like many things, picking out pumpkins is really more about the journey than the destination. The true fun is in savoring the scenery and enjoying the crisp fall air — which can be done from Butler’s Orchard, one of the most popular spots within an hour’s drive of DC to pick pumpkins and sip apple cider (not to mention the site of our fall team get-together)! Craving another option? Queen Anne Farm is also a great choice.

#5 Sample Wine In A Historic Setting: From October 10th-12th, taste unlimited samples from Virginia wineries and enjoy the sunset over the Potomac River after hours at George Washington’s storied estate. Bring a blanket or reserve a VIP table and relax on the east lawn. Hear live music by Bruce Ewan and the Solid Senders, and enjoy concessions available for purchase from the Mount Vernon Inn Restaurant.

Fall is one of our favorite seasons in DC! Check out these related blogs for more recommendations!

#6 Raise A Stein To Oktoberfest: It’s official: DC is bringing back its annual Oktoberfest celebrations, starting on Saturday, September 20th, and running through Sunday, October 5th. Upcoming Prost-hosted events include a kick-off at MVT Farmfresh Market (where festive brews meet fresh produce), a German beer and tasting class, a happy hour, and a slew of other themed activities. For more German-style festbiers and Bavarian-inspired foods, look no further than Wunder Garten, which will be transformed into a lively 4-week celebration that blends classic German traditions with DC’s best local entertainment, food, and drinks. And starting October 4th, the Wharf is the place to be when you feel like raising a Stein — events include the Dachshund Dash, Polka on the Pier, and more.

Planning to fit in a move this fall — between your jam-packed lineup of festivities, that is? Get in touch with us directly by calling 202.280.2060 or emailing us at connect@jennsmira.com today!