Downtown Leesburg is so charming with its brick sidewalks, historic buildings dating back to the 1700s, and locally-owned shops. There is plenty of shopping – Isabel's favorites are Zest, The Global Local, and Creme de la Creme. For drinks and bites, try Sidebar (great happy hour!), King Street Oyster Bar for fresh seafood, or Fireworks Pizza for casual dining. For coffee, our favorites are Side Bar and Second Nature Coffee Co.

Buford's Biscuits: Beloved breakfast and brunch spot with Southern-style biscuits and comfort food

SideBar Coffee: Great coffee and pastries in downtown Leesburg

Second Nature Coffee Co.: Specialty coffee and welcoming atmosphere

King Street Oyster Bar: Fresh seafood and raw bar in the heart of downtown

Fireworks Pizza: Casual spot for pizza and Italian favorites

Monks BBQ: Casual barbecue with great outdoor seating

Tuscarora Mill ("Tuskies"): Upscale American in a restored mill building. Also the wedding caterer!

Lightfoot Restaurant: Farm-to-table fine dining in a historic bank

Sidebar: Creative cocktails and upscale small plates (seriously, the best happy hour deal)

Bear Chase Brewing Company: Excellent selection with a welcoming taproom atmosphere

Crooked Run Brewing: Excellent IPAs and sours, plus a taproom in downtown Leesburg

Black Hoof Brewing Company: Small-batch beers in downtown Leesburg

Catoctin Creek Distilling Company: Virginia's first legal distillery since Prohibition—try their Roundstone Rye whiskey

DMV Happy Hours: Check out Steven's website to find local happy hours

Loudoun County is home to over 40 wineries, many just minutes from Leesburg. Our top picks:

Bluemont Vineyard: Great mountain views and live music on weekends

Sunset Hills Vineyard: Stunning views, excellent Chardonnay and Cabernet Franc

Fabbioli Cellars: Family-owned with a relaxed atmosphere and great Sangiovese

Chrysalis Vineyards: Known for Norton (Virginia's signature grape) and beautiful grounds

Stone Tower Winery: Elegant tasting room with panoramic views

Smithsonian National Air and Space Museum Udvar-Hazy Center (20 minutes): Incredible collection of aircraft and spacecraft including the Space Shuttle Discovery, SR-71 Blackbird, and the Enola Gay. Free admission ($20 parking). A must-see for aviation enthusiasts!

Harpers Ferry, WV (30 minutes): Historic town where the Potomac and Shenandoah rivers meet. Walk the historic lower town, hike Maryland Heights for incredible views, or try tubing/rafting on the Shenandoah

Great Falls Park (25 minutes): Dramatic waterfalls and hiking trails along the Potomac—arrive early on weekends as it fills up

Downtown Washington, DC (50 minutes): Smithsonian museums (all free!), monuments, and world-class dining