In the heart of Loudoun County, a multitude of bustling stores, boutiques, restaurants, cafés, and cultural attractions line the streets of downtown Leesburg. The picturesque, historic town is a hub for local businesses and a perfect weekend destination.
The walkability of the area allows people to park their cars in one of five nearby parking garages and stroll around town, admiring the brick exteriors of the charming storefronts.
Small businesses abound, from vintage clothing boutiques and gift shops to eclectic bookstores and record shops. More than 40 dining and drinking establishments cater to a variety of cuisines and preferences. Whether you’re looking for sweet or savory options, coffee or beer, or vegetarian-friendly selections, there’s no shortage of options.
Read ahead for our picks for shopping, dining, and entertainment in downtown Leesburg.
Shopping
Birch Tree Bookstore
Peruse classic books and new releases while exploring a curated selection of houseplants at this independent bookstore and plant shop. Birch Tree Bookstore and Foliage Plant Shop are connected in this quaint woman-owned store that appeals to readers and plant enthusiasts alike. 11 W. Market St., Leesburg
Dig! Records & Vintage
From classic Fleetwood Mac records to Taylor Swift’s discography, Dig! Records & Vintage has it all. Customers can buy, sell, and trade records and shop for CDs, tapes, sleeves, players, amps, and more. 212C Loudoun St. SE, Leesburg
Misguided Angels
This women’s clothing store also carries shoes, handbags, and jewelry from up-and-coming designers. Shop for bold belts and boho dresses, or explore the store’s quirky selection of custom hand towels. 14 S. King St., Leesburg
Medlin Art Gallery
For over 35 years, this fine art and custom framing establishment has specialized in high-quality framing and prints. The gallery represents local, national, and international artists, and offers a wide selection of original paintings, antique prints, and engravings, along with hundreds of frames. 2 Loudoun St. SE, Leesburg
Muz & Rose
This bright boutique features timeless patterns and modern touches in its clothing, bags, accessories, and home finds. The collective of vintage sellers and independent artists includes the eco-friendly Flores & Terram, Nico Plaza, and Vintage Bride Home. 3 Loudoun St. SW, Leesburg
The Lucky Knot
Whether you’re looking for outfits for your next beach trip or just pieces to spruce up your summer wardrobe, this Southern-style coastal boutique is your one-stop shop. The blue, pink, and white color palettes of dresses, blouses, skirts, and menswear are perfectly preppy, and there are more than 30 brands to choose from. 9 N. King St., Leesburg
Very Virginia Shop
Explore all things Virginia at this store featuring gourmet foods, spices, BBQ sauces, souvenirs, décor, and more. Try some local honey and peruse college alumni and history memorabilia, ideal for gift-giving. 16 S. King St., Leesburg
Dining
Black Hoof Brewing Co.
This German-themed brewery offers a constantly changing drink lineup of German lagers and European ales and an inviting taproom to try the delicious brews. Soft Bavarian pretzels are available to purchase, and they allow patrons bring in outside food if they wish to. 11 S. King St., Leesburg
Cowbell Kitchen
A farm and local producer-driven eatery, this charming breakfast and lunch spot features sweet and savory options and organic, vegetarian-friendly food. Enjoy housemade baked goods and pastries or grain bowls and fresh sandwiches on covered outdoor patio seating. 26 N. King St., Ste. 110, Leesburg
Fire Works Pizza
This wood-fired pizza restaurant and bar has been a Leesburg staple since 2006, serving up fresh salads and sandwiches, signature and custom pizzas, and a variety of craft beers on draft. The friendly staff accommodates any allergies or dietary preferences. 201 Harrison St. SE, Ste. 200, Leesburg
Leesburg Diner
Established in 1865, this diner still retains its retro interior with checkered flooring, a tabletop bar, and electric guitars on the walls. The restaurant offers classic American fare for breakfast and lunch, including milkshakes and brunch cocktails. Try a cheeseburger or a poutine skillet. 9 S. King St., Leesburg
Mom’s Apple Pie Company
This small but tasty pie shop is dedicated to baking natural preservative-free pies with quality fruit including strawberries, raspberries, blackberries, and rhubarb. The store also features housemade breads, cookies, buckeyes, and lemon bars. 220 Loudoun St. SE, Leesburg
Señor Ramon
Authentic street-style Mexican food is distinct to this taquería that opened in 2016. Enjoy tacos, bowls, nachos, and specialty empanadas all made with the freshest ingredients. This location is one of five in NoVA. 38 S. King St., Leesburg
Entertainment
Loudoun Museum
To learn more about the county’s history, visit the Loudoun Museum to explore culture and natural treasures for free. Current exhibits include Caught in the Maelstrom of Civil War: Loudoun County Divided, A Fragile Republic: 1800-1825, and Vintage Pursuits: Cultivating a Virginia Wine Industry. Behind-the-scenes tours and virtual exhibits are available. 16 Loudoun St. SW, Leesburg
Summer JAMS Concert Series
Throughout the summer until August 17, downtown Leesburg hosts free summer concert series every Saturday. Entertainers include Sela Campbell, Pebble to Pearl, and Justin Trawick and The Common Good. Bring lawn chairs and blankets to set up a picnic while you watch the shows on the Town Green. 25 W. Market St., Leesburg
Feature image by Mallory Evans
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