Things to do in Leesburg
Discover amazing Leesburg activities and premium in-home experiences.
Leesburg, where rich history meets contemporary charm, offers a delightful blend of past and present. Explore the beautifully preserved downtown with its quaint shops and vibrant local eateries or take in the scenic countryside dotted with award-winning wineries. This charming town invites visitors to experience both culture and comfort away from bustling city life.
Popular Activities in Leesburg
E-Bike Rentals in Herndon, VA
Explore the W&OD Trail with easy pedal assist on flexible half or full day rentals
E-Bike Rentals in Leesburg on the W&OD Trail
Explore the scenic W&OD Trail with pedal assist and throttle; helmet and lock included
Wine and Chocolate Tasting at River-Sea Chocolate Factory
Sample five craft chocolates paired with three wines while learning bean-to-bar techniques
Craft Chocolate Tasting Flight
Taste five single-origin chocolates and learn the bean-to-bar process
Private Winery Tour in Sonoma County
Experience the best of Sonoma's wine country with our Private Winery Tour Service. Travel in style with up to 6 passengers, as our expert guides whisk you away on a bespoke 6-hour tour of three hand-picked wineries.
National Mall Memorials and Monuments Walking Tour
Explore iconic DC memorials with a licensed guide on a focused 2-hour walk
Georgetown Walking Tour in Washington DC
Trace Georgetown's evolution from gritty port to elite enclave on a guided 2-mile walk.
Private DC Architecture Tour with Expert Guide
Discover DC's architecture and history on a flexible, guide-only private tour.
Whitewater Tubing on the Potomac at Harpers Ferry
Ride beginner Class I–III rapids with shuttle access and scenic Potomac River views
Whitewater Rafting on the Shenandoah and Potomac
Tackle Class I–III rapids with a guide and enjoy a private take-out with shuttle
Flat Water Tubing on the Shenandoah River
Relax on an easy float with shuttle service and an all-day tubing pass
Harpers Ferry Inflatable Waterpark Session
Bounce, climb, and race across giant inflatables in a scenic quarry during a 1.5-hour session
Guided Harpers Ferry Whitewater Rafting
Tackle Class I–III rapids on the Shenandoah and Potomac with expert guides near DC and Baltimore
Guide Assisted Whitewater Kayaking
Paddle inflatable kayaks with a guide through Shenandoah and Potomac rapids
Single Kayak Rental at Fletchers on the Potomac
Paddle the Potomac at your own pace with gear included
Stand Up Paddleboard Rental at Fletchers
Glide the Potomac on an easy, scenic SUP escape with included gear
Double Kayak Rental at Fletchers
Enjoy a sit-on-top double kayak rental for 1 to 4 hours with gear included
Canoe Rental at Fletchers on the Potomac
Paddle the Potomac from Fletchers in a stable canoe for a peaceful city escape
Rowboat Rental at Fletchers
Set your own pace on the Potomac for fishing, picnics, and peaceful views.
Beach Cruiser Bicycle Rental at Fletchers
Explore the C&O Canal Towpath or Capital Crescent Trail on an easy-to-ride beach cruiser
Cleveland Park & National Cathedral Grounds Tour
Stroll historic Cleveland Park and explore National Cathedral grounds on a 2-hour guided walk
Explore the Charm of Leesburg
Leesburg offers a delightful blend of history, charm, and modern vibrancy that invites visitors to explore its unique character. Known for its well-preserved historic district, Leesburg provides a picturesque setting with cobblestone streets lined by 18th-century buildings housing boutique shops and inviting cafes. As you wander through town, you'll discover an array of local eateries serving farm-to-table dishes that reflect the region's agricultural heritage.
The surrounding countryside is dotted with wineries and breweries offering tastings set against scenic backdrops. A visit to Morven Park or Oatlands Historic House & Gardens reveals beautifully manicured landscapes perfect for leisurely strolls or picnics in warmer months. For those who love outdoor adventures, nearby trails like the Washington & Old Dominion Railroad Regional Park provide excellent opportunities for biking or hiking amid Virginia’s natural beauty.
Leesburg stands out from other destinations due to its rich tapestry of past meets present experiences—where Civil War sites coexist alongside vibrant farmers markets and cultural festivals throughout the year. Whether you're exploring art galleries during First Friday events or savoring seasonal flavors at local restaurants, Leesburg promises memorable moments steeped in both tradition and innovation.