When Whitlow’s on Wilson opened at the corner of Wilson Boulevard and North Fillmore Street in November 1995, Clarendon wasn’t quite a nightlife destination. The handful of bars — including Galaxy Hut, Strangeways, the Bardo Rodeo and Blue and Gray brewpubs — served a neighborhood crowd, while Iota offered nightly live music. The view from Whitlow’s was very different than it is now.

“That corner where the Cheesecake Factory is was a garage,” says manager Jon Williams, pointing across the street. “I used to park there and get my oil changed. There used to be a farmhouse where the Barnes and Noble is.

“It was a different neighborhood — a little more funky, a lot more independent.”

Two decades on, Whitlow’s remains a cornerstone of any conversation about bars in Arlington, thanks to its $3 happy hours, tiki-themed rooftop deck and live music. This weekend, the bar marks its big anniversary with two nights of parties. Celebrations begin Friday with the release of Whitlow’s Good Time IPA, a one-time-only beer brewed by Devils Backbone. Saturday features a free concert by Virginia Coalition, the local rock and funk band that was a fixture at Whitlow’s in the early 2000s before moving on to headline larger venues.

The history of Whitlow’s is much longer than its time in Clarendon: It originally opened downtown at 11th and E streets NW in 1946 as a greasy spoon and bar where “third-shift workers sat next to judges, and everybody was copacetic,” Williams recalls. His stepfather, Greg Cahill, purchased Whitlow’s in 1971 and ran it until 1989, when the entire block was torn down to make way for theaters and an office building.

Whitlow’s planned to reopen in the new building, but an economic downturn meant that development stalled for years, so Cahill eventually relocated Whitlow’s to a former furniture showroom on Wilson Boulevard. He decorated it with mementos and signs from downtown, including the neon sign that adorned the Crown Bar and Grill and a brass plaque that hung at the Woodward and Lothrop department store. (Another sign, from Whitlow’s neighbor M.E. Swing, went back to the coffee shop a few years ago.) The church-pew seating came from St. Patrick’s Church, around the corner from the original Whitlow’s, where Cahill was a parishioner.

As the years went by and the number of condos grew in the neighborhood, Williams says, the crowds got younger, and the jazz and blues performed on the shoebox-sized stage were replaced by cover bands and DJs. The bar expanded into a former sign shop next door to create the beach-themed Sand Bar in 1998, and then upwards to the rooftop in 2011. Williams says the thatched-roof bar on the deck will begin hosting monthly luaus and pig roasts later this year.

Whitlow’s made its mark early with promotions that continue today: half-price burgers, currently available Mondays from 11 a.m. to 11 p.m., and Mug Night, which allows customers to get $2 beers once they’ve purchased a $5 Whitlow’s Mug. When Mug Night started, “I’d just gotten out of college and was learning how to bartend,” Williams says. Customers would bring their own “mugs” from home, including “buckets and Big Gulp cups,” he recalls. “We had to reel that in.”

For Williams, this is a weekend for looking forward as well as back. Whitlow’s increased its draft lines to 24 so that it could offer more craft beers, and Williams looked into adding a small brewery before deciding that it wasn’t possible because of limited space. Instead, he’s hoping to work with Virginia breweries on a series of exclusive beers. The first one, from Devils Backbone, is a single-hopped Citra IPA, and just 4.7 percent alcohol by volume. It will be tapped Friday at 7 p.m., with food and drink specials until 9 p.m.

On Saturday, the party flashes back to the early 2000s. Before Virginia Coalition built a legion of followers and began selling out the 9:30 Club and Birchmere, they regularly performed at Whitlow’s on Tuesday nights, alongside such up-and-comers as SOJA (then known as Soldiers of Jah Army) and Carbon Leaf. “The guys in VaCo and SOJA were like, ‘We can do this for a living?’ And then they went off to play the 9:30 Club,” Williams says. (That they chose Whitlow’s wasn’t a surprise: Virginia Coalition singer Andrew Poliakoff was a server at the bar at the time.)

“I don’t know if the younger people will know who they are, but I’m psyched,” Williams says. “It should be a great way to celebrate a weekend.”

If you go
Whitlow’s on Wilson

2854 Wilson Blvd., Arlington. 703-276-9693. whitlows.com.