Festive Fun Near You: The Best Things to Do This Holiday Season Around Loudoun, Fairfax, Montgomery, D.C., and Beyond

Festive Fun Near You: The Best Things to Do This Holiday Season Around Loudoun, Fairfax, Montgomery, D.C., and Beyond

The holiday season has officially arrived, and with it comes twinkling lights, cozy markets, and festive fun in every corner of the D.C. metro region. Whether you’re sipping wine by a fire in Loudoun County, exploring light displays in Fairfax, or strolling through a historic downtown in Fredericksburg, there’s something magical waiting nearby.

Here’s your guide to the best local holiday events across Loudoun County, Frederick County, Montgomery County, Fairfax County, Washington D.C., Arlington County, Spotsylvania County, and Fredericksburg, Virginia.

 

Loudoun County, VA

From charming small towns to scenic vineyards, Loudoun County knows how to celebrate the holidays in style.

 

  • Christmas in Middleburg: One of the region’s most beloved holiday traditions, this two-day event includes a festive parade, tree lighting, and holiday shopping throughout the village.

  • Leesburg Holiday Fine Arts & Crafts Show: Find one-of-a-kind gifts from local artisans while enjoying live music and holiday treats.

  • Winery Holiday Weekends: Many Loudoun wineries host themed brunches, cocoa bars, and ornament-making events - perfect for a winter weekend getaway.

  • Don’t miss: Strolling through downtown Leesburg after dark to see the glowing lights and historic storefronts all decked out for the season.

 

Winchester, VA

Step into a storybook setting in Winchester!

 

Frederick, MD

Frederick, Maryland shines bright during the holidays, combining historic charm with modern festivities. Stroll along Downtown Frederick’s beautifully lit streets, where brick sidewalks, twinkling lights, and decorated shop windows create the perfect holiday postcard.

  • Kris Kringle Procession: A beloved local parade through downtown Frederick featuring floats, costumed characters, and a visit from Santa himself.

  • Holiday Makers Market at the Delaplaine Arts Center: Browse handmade gifts, ornaments, and art from local creators — perfect for unique holiday shopping.

  • Carols by Candlelight: Join the community for an evening of carols, candles, and celebration in the heart of historic Frederick.

  • Carroll Creek Park Sailing Through the Winter Solstice: Perhaps the most magical of all - dozens of illuminated sailboats float down Carroll Creek, creating a stunning, one-of-a-kind light display.

  • Why go: Frederick offers big holiday spirit with small-town warmth. Between the lights, markets, and music, it’s the kind of place that makes you slow down and truly savor the season.

 

Montgomery County, MD

Just over the Potomac, Montgomery County offers plenty of festive fun for Maryland locals and visitors alike.

 

Fairfax County, VA

Fairfax County lights up the night with classic events that have become local favorites.

 

Washington, D.C.

The nation’s capital transforms into a festive playground during the holidays.

  • National Christmas Tree & Pathway of Peace: Visit the Ellipse near the White House to see the iconic tree and state-themed decorations.

  • Downtown Holiday Market: Located on F Street NW, this outdoor market features artisans, food vendors, and live entertainment.

  • Winter Wonderfest at Nationals Park: Nationals Park will transform into Washington DC’s headquarters for all things thrilling, chilling, and fantastically fun.

  • Why go: D.C. delivers the magic - from grand monuments aglow to cozy corners filled with carols and cocoa.

 

Arlington County, VA

Small but mighty, Arlington celebrates with community charm.

 

Spotsylvania and Prince William Counties

Experience the holidays the way they’re meant to be — community-centered and full of heart.

  • Spotsylvania Christmas Parade: A cherished local tradition featuring floats, marching bands, and, of course, Santa Claus.

  • A Stafford Holiday: Lights, music, and holiday treats create a nostalgic small-town feel.

    • Why go: It’s festive without the fuss — a perfect family-friendly outing that feels like stepping into a Hallmark movie.

  • Mistletoe Holiday Craft Festival: Visit the Montclair Library for vendors selling crafts, jewelry, and more. A "jolly visitor" will be in the children's area, and a Story Time with Santa

 

Fredericksburg, VA

Historic charm meets holiday cheer in Fredericksburg.

  • Christmas Parade: A can’t-miss event along Caroline and Princess Anne Streets featuring dozens of floats and community groups.

  • Holiday Carriage Rides: Cozy up for a Victorian-style ride through Old Town’s cobblestone streets.

  • While you’re there: Explore the downtown shops for unique gifts and grab dinner at one of the town’s many festive restaurants.

 

Celebrate the Season Locally

From twinkling lights to time-honored traditions, the Mid-Atlantic region offers endless ways to make this holiday season magical. Whether you’re exploring a new town or returning to a favorite local tradition, there’s no better way to celebrate than by supporting local events and communities.

So grab your coat, pour some cocoa, and make this holiday season one to remember - right here at home.

 

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