Cocktail Crawl: Can’t-Miss Summer Sips in Middleburg
Written by Kaitlin Hill
As temperatures continue to rise, July is the perfect time to sample the best cocktails just off Washington Street. From a mint-infused Southside at Mt. Defiance to Lost Barrel’s fruit-forward Summer Fizz, there is something for everyone in Middleburg’s bars inspired by local ingredients, creative culinary skills, and twists on the classics. To experience them all, follow our cocktail crawl and you might just discover your new signature sip for the summer!
The Southside at Mt. Defiance Cidery & Distillery
495 E. Washington Street, Middleburg, VA 20117
Head around to the back of the barn to grab a Southside cocktail at Mt. Defiance Cidery & Distillery. Made with the house Gin Nouveau, lime, lemon, simple syrup, and fresh mint, the cocktail is light and refreshing with a punch of citrus flavor. The drink is so popular, guests at Mt. Defiance are likely to see a few of the vibrantly green drinks down the length of the bar.
Jarad’s Gin & Tonic at Tremolo Bar
19 E. Washington Street, Middleburg, VA 20117
When asking for recommendations around town, Jarad’s Gin & Tonic at Tremolo Bar was a frequent suggestion. Described by one patron as “fresh, sharp, light, and refreshing,” Jarad Slipp’s take on a classic G&T is made with gin, tonic, lime, orange, and botanicals. Served in a wine glass, the drink is as generous as it is delicious and the perfect thing to nurse on a warm evening in Middleburg.
The Clark Kent at The Red Fox Inn & Tavern
2 E. Washington Street, Middleburg, VA 20117
Created by James Spencer, Red Fox Inn & Tavern hospitality team member, the Clark Kent is bursting with local summer flavors. A shaken concoction of local gin, fresh strawberry-basil puree, fresh lemon juice, and a little bit of local honey, this pink drink is sweet, herbaceous, and extremely refreshing. Red Fox’s director of food and beverage, Anna Adams, shares that it is the most popular cocktail on the menu right now.
Classic Old-Fashioned at Nomad
14 S. Madison Street, Middleburg, VA 20117
Just steps off of Washington Street, Nomad is serving seriously tasty bourbon in its laid-back bar and expansive patio. The old-fashioned is made with Sazerac rye whiskey and garnished with orange peel and a cherry. While an old-fashioned may not be the first drink that comes to mind for a summer sip, Nomad’s is smooth with the perfect amount of sweetness.
Margaritas at Bluewater Cocina
12 S. Pendleton Street, Middleburg, VA 20117
Follow the smell of sizzling tacos behind Nature Composed to Middleburg’s own little taco bar in a garden. The margaritas at Bluewater Cocina are the perfect ice-cold cocktail to be enjoyed on a hot summer day. The margaritas come in four iterations: classic, fresca, garden jalapeño, and skinny. In the summer, the seasonal fresca is strawberry-flavored with a dollop of strawberry puree on top. Made with in-house strawberry mix, triple sec, and Luna Azul, the fresca margarita packs a punch.
The Summer Fizz Mimosa at Lost Barrel Brewing
36138 Little River Turnpike, Middleburg, VA 20117
Stay on Route 50 just past town for the final cocktail in the crawl, Lost Barrel Brewing’s Summer Fizz Mimosa. A crushable combination of pineapple, lime, orange, watermelon puree, and simple syrup, the Summer Fizz makes the drive worthwhile. Lost Barrel also offers a mocktail version of the Summer Fizz, meaning this summer drink can be enjoyed by all. ML
Featured photo: The fresca margarita at Bluewater Cocina. Photo by Kaitlin Hill.
Published in the July 2025 issue of Middleburg Life.