How to Welcome Fall in DC

Posted on September 8, 2026 | Posted in Lifestyle
How to Welcome Fall in DC
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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 brimming with vibrant vignettes layered with spellbinding attractions…and we’re here to help you experience the season’s best until the very last leaf falls.

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

Hoping to make a real estate move before Winter arrives? Click here to read our blog about selling your home before the end of the year.

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.

Celebrate Snallygaster

Those in the know will know: Snallygaster is the District’s biggest beer festival, bar none. And on October 10th, the merry monster returns to DC for its 13th year and 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.

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 29th-November 1st 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:


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.

Sample Wine In A Historic Setting

From October 9th-11th, 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 Johnny Burgin Blues Band, 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!


Raise A Stein To Oktoberfest

Raise a stein to Oktoberfest season with celebrations popping up all across DC. Kick things off at Wunder Garten in NoMa on September 18th, where traditional keg tapping, German-style beers, and live music bring a taste of Bavaria to the District.

Then on September 26th, the Great Oktoberfest Crawl takes over Dupont Circle with themed drink specials, giveaways, and a Bavarian costume contest. Next, head to District Pier on October 3rd for Oktoberfest at The Wharf, DC’s biggest free Oktoberfest celebration featuring the Wiener 500 Dachshund Dash, a stein-hoisting championship, polka dancing, and plenty of Sam Adams Oktoberfest beer. Prost!

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!

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