The best local bars for each drinking decade

C&O’s barnwood-paneled downstairs bar is like a speakeasy without the secret knock. Photo by Stephen Barling C&O’s barnwood-paneled downstairs bar is like a speakeasy without the secret knock. Photo by Stephen Barling

By Pen + Knife bloggers

For generations, authorities have buried the lede when warning us about alcohol killing brain cells. Omitted from the tired mantra is the truth that some of our deepest seeds of wisdom are sewn at watering holes and colored by booze. Bars are like classrooms, just more practical, and the life lessons enduring. No matter our demographic, we’re still learning in our 20s, 30s and 40s from a barstool perch. Thankfully, the local scene is abundant with venues for every age bracket. Let’s bar crawl through a few of our favorite decade-appropriate spots.         

Your 20s: Parallel 38

Get your first round at Parallel 38 on West Main Street—a reasonable distance from the Corner and college days (because you’re an #adult now), while still close enough for security blanket purposes. Your new booze cravings are thoughtful cocktails with carefully selected ingredients that your mom’s herb garden would approve of. The downstairs bar at Parallel is perfectly low-lit, has an intimate, sophisticated NYC vibe and is ideal for drinks with the gals or a first post-grad Bumble date. Chat up owner Justin Ross if he’s buzzing around for rich stories of his past life in Washington, D.C., training under internationally acclaimed restaurateur José Andres and the renovation work that went into the recently relocated P38 space. If temps are in your favor, head to the back porch for some open-air imbibing, Mediterranean small plates and to people-watch Amtrak passengers below.

“Um, a cranberry vodka?”: Stop that. You’re past cranberry vodka and ending your drink orders with question marks. Try instead the Akrotiri Heat (Espolòn blanco tequila, piri piri syrup cinnamon berry, hibiscus soda, citrus), a multi-layered cocktail we’ve come to crave, and a P38 staple.

Grape expectations: Wine it up here. Ross, a certified advanced level sommelier, has assembled one of the most extensive and unique by-the-glass wine lists in town, which will allow you to explore your emerging adult palate without breaking the bank.

Alternatives: The Whiskey Jar, Oakhart Social

Your 30s: The Alley Light

This is the decade when you should enrich your cocktail game with sophistication and nuance. Duck into The Alley Light, a clandestine speakeasy nestled in an alley off the Downtown Mall, designated only by a lantern over the door. Dig the mysterious vibe as you ascend stairs to the cozy dark space and behold a wonder wall of obscure spirits. Nervous? Don’t sweat it, because affable AF barman Micah LeMon has mastered the art of baptizing newcomers to the craft. (This cat literally wrote the book on it—The Imbible.) Trouble can’t find you here, so sit back and submit to the spellbinding white noise of booze and ice dancing in the shaker and know that whatever he’s pouring will spike your night with intrigue.

Prime time: Show up pre-dinner rush (5ish) to score a stool and charming conversation with LeMon—it’s basically a TedX talk on mixology.   

Nosh away: Some of the best food in town is right here, and LeMon excels with pairings. Our go-to is foie gras brûlée with The Doctor’s Orders.

Alternatives: Lost Saint, Brasserie Saison, Mas

Your 40s: C&O

By your 40s, if you’re doing it right, you know what you like and don’t bother much with trends. This lands you in the cozy confines of the C&O’s bistro bar. Down a set of creaky stairs, this rustic barnwood-paneled room has harbored sophisticated imbibers for 42 years with a soulful charm achieved through slow, honest evolution. Permeating the scene is a secret society vibe that grips you immediately as you settle in. Behind the stick, clad in dope vintage gear, you’ll find some of the most thoughtful, kind booze-slingers in the business, who will happily guide you through a treasure trove wall of spirit options or their spot-on list of house cocktail creations. We are partial to the Jota Jota, a jolting riff on a drink near and dear to us, the Boulevardier. Whatever your poison, raise that glass to the next 40—yours and theirs—alongside friendly ghosts of patrons past in this landmark watering hole.

Discovery zone: Barman Anthony Restivo curates an eclectic playlist you’ll want to poach from.

Sneaky legit: Hiding out on the late-night menu (after 10pm) is one of the best burgers around for only $6.

Alternatives: Tavola’s Cicchetti Bar, Common House, The Coat Room

Pen+Knife is a blog that celebrates the bounty of food, drink and life in Charlottesville.

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