Eight Bars, One Bourbon: The Old Town on the Rocks Challenge

A Toast to Community Spirit

Winchester's Old Town district is shaking off the post-holiday blues with a spirited comeback. In this episode of The Valley Today, host Janet Michael and Brady Cloven, Executive Director for Friends of Old Town, recently embarked on what they jokingly called "research"—a Friday afternoon bar crawl previewing Old Town on the Rocks, a revived cocktail competition set for January 16-18, 2026.

The event marks the return of a beloved tradition that disappeared during COVID. After a five or six-year hiatus, Brady and his team approached the original organizers to revive the competition. "They said, cool, we'll give you the ownership of it. Do what you want with it," Brady recalls with a laugh. 

A New Focus on Main Street

This year's competition takes a more focused approach than its predecessor. Rather than spreading across the entire city, Old Town on the Rocks concentrates exclusively on the Old Town Walking Mall and Main Street district businesses. "We're the Main Street Program and our region and our scope is the Old Town District," Brady explains. While future years may expand to include establishments like Oak Stone or Crush, this inaugural revival keeps things tight and manageable.

The strategy serves a dual purpose: showcasing the creativity of local bartenders while driving business during one of the slowest months of the year. "Everybody backs off from being out after the holidays," Brady notes, "but this is trying to push them through for a weekend and say, hey, there's still things to do down here."

Stop One: Hideaway Cafe's Coffee Cocktail Mastery

The duo begins their journey at Hideaway Cafe, where co-owner Greg Armstrong has transformed a coffee shop into an unexpected cocktail destination. Located in the big green building on the corner of Cork and Loudoun—the old Bargain Corner for longtime Winchester residents—Hideaway boasts a unique advantage: a full espresso bar alongside its liquor license.

Greg's background reveals a passionate hobbyist turned professional. Years ago, he took a bartending course as a gift, but his instructor quickly realized Greg's extensive knowledge. "The guy who was teaching the course realized that he would go through what was in the text, and then turn to me and say, what do you know about it?" Greg remembers. "And I would talk for half an hour about whatever it was."

The Long Winter's Night Manhattan

For the competition, Greg crafted the Long Winter's Night Manhattan, a sophisticated twist on the classic Black Manhattan. Instead of traditional vermouth, he uses Amaro—an Italian botanical liqueur—then adds Licor 43 (Cuarenta y Tres), a Spanish cordial with 43 infused botanicals that brings vanilla and citrus notes. A touch of Amarena syrup rounds out the cherry flavors.

"It's got really good flavor," Brady observes after his first sip, noting the lingering spice from the whiskey and botanicals. Janet agrees enthusiastically, remarking that the alcohol doesn't overpower the complex layers—a common pitfall in bourbon-forward drinks.

Greg's bar operates on an unconventional schedule. Patrons can order cocktails from 9 AM until closing, though Greg admits morning orders tend toward Irish coffees and espresso martinis. The cafe closes Mondays for administrative work, opens 9-2 on Tuesdays, 9-5 Wednesday through Saturday, and 9-4 on Sundays. Special evening events extend hours to around 7 PM, all posted on their Facebook page.

Stop Two: V2's Nerdy Indulgence

Next, Janet and Brady head to V2, where GM/bar manager Courtney has prepared something entirely different. The restaurant, which has anchored Old Town for 23 years, recently expanded its beverage program and just secured an ABC license for its sister restaurant, Mangia Cucina Italiana.

Courtney's creation, the Red Eye Mordor, draws inspiration from an unexpected source: the 25th anniversary re-release of Lord of the Rings, screening the same weekend as the competition. "I'm a huge Lord of the Rings fan, as well as my boyfriend," Courtney explains. "I kind of just wanted something that inspired me from the movie, plus to kind of nerd out with it."

A Coffee-Based Journey to Middle Earth

The cocktail combines coffee with a hint of spice, referencing Frodo's sleepless journey into the fiery realm of Mordor. Edible gold glitter symbolizes the One Ring, while red glitter on top adds visual drama. When Janet admits she's never seen Lord of the Rings, Brady looks genuinely shocked. "This drink is literally going to be my introduction to Lord of the Rings," she laughs.

After tasting, Brady's eyes widen. "Oh my gosh, it's like a spiced hot chocolate," he exclaims. "It lingers a lot in a good way." Janet agrees, noting that even non-coffee drinkers would appreciate the balanced flavors.

Courtney's creative process involves considerable trial and error—and drinking. While developing the Red Eye Mordor, she struggled to identify a missing ingredient, complicated by recovering from illness. "Two days I'm stewing on this," she recalls. "I finally figured it out. I'm not gonna say 'cause it's a secret ingredient, secret recipe."

Beyond the competition, V2 offers an extensive menu featuring fresh pasta and a growing tequila collection. Their happy hour runs 4-6 PM Monday through Friday, with a special Saturday morning happy hour featuring dollar oysters. The restaurant operates 11:30 AM to 9 PM Monday through Saturday.

Stop Three: Roma's Warm Surprise

The final stop brings Janet and Brady to Roma, known primarily for pizza but hiding a sophisticated bar program. Chris, the bartender who created the competition entry, isn't present, but his Smooth Like Butta cocktail speaks for itself.

This drink stands out as the only warm cocktail in the competition—a bold choice that initially makes Brady hesitant. "I'm not a huge fan of warm drinks," he admits. The cocktail features Elijah Craig Rye, house-infused apple brandy, house citrus shrub, and a touch of butter.

Defying Expectations

After the first sip, Brady's skepticism evaporates. "Oh, that is smooth like butta," he marvels. Janet, equally impressed, confesses her initial doubts: "I had my doubts, but all of my doubts have now been erased. This is amazing."

The butter element proves particularly striking. "It even tastes like butter," Janet observes. "After you're done, you can feel it on your lips." Brady nods enthusiastically, calling the experience "insane."

The warm cocktail's timing couldn't be better. While the preview happens on a mild 60-degree rainy day, the actual competition weekend will likely bring temperatures in the 30s or 40s—perfect weather for a warming drink.

The Competition Framework

Old Town on the Rocks features eight participating establishments: Hideaway Cafe, Roma, V2, Wine Room, TT Walls, The Half Note Lounge, Bistro Sojo, and Uno's (located under the George Washington Hotel). Each venue creates a unique cocktail using Elijah Craig bourbon, courtesy of sponsor Heaven Hill.

The competition runs two parallel tracks. A panel of four judges—including Charlie Fish, one of the original Winchester on the Rocks organizers—will evaluate drinks using a standardized rubric. The winner receives a trophy provided by Elijah Craig. Simultaneously, fan voting occurs via QR codes at each location, determining the People's Choice winner.

"I think it's a good way to have four judges who are all very interested in Old Town and live here, work here," Brady explains. However, Janet acknowledges that many restaurants value the popular vote even more than the judges' trophy. "They wanna know how many votes did they get as the most popular. That means a lot more to them sometimes."

Heaven Hill Distillery and Elijah Craig stepped up as sponsors after Brady reached out following a suggestion from Caleb at Roma. "Just like that we did and they came and we had a conversation," Brady recalls. "I said, here's what we're thinking. They said, we'd love that idea."

Beyond the Bourbon

The event serves a larger mission for Winchester's Main Street Program. Brady pushes back against the perception that Old Town hibernates during winter months. "I don't think that Old Town goes into hibernation mode," he insists. "I think you just have to really look, and there are a ton of things that we have that can pull you indoors."

He points to four museums within walking distance, an emerging arts district featuring Typewriter Studio and Polka Dot Pot, and the ongoing holiday market at ShenArts. "There is always something to do when it gets colder," Brady emphasizes. "You just still look a little harder, and we're hoping to push that forward."

The timing also addresses a critical business challenge. January represents a financial lurch for small businesses—customers are waiting on tax returns, recovering from holiday spending, and generally reluctant to venture out. "It's still very important to support your small businesses," Brady urges. Even those who can't attend can help by sharing event information on social media.

A Culinary Hub's Diversity

Throughout their afternoon journey, Janet and Brady repeatedly note Old Town's remarkable diversity. "Everything is very unique down here," Janet observes. "You're not gonna walk up and down the mall or even on the ancillary parts and find exactly the same thing."

The three cocktails they sample prove her point. From Hideaway's sophisticated Manhattan variation to V2's nerdy espresso martini to Roma's buttery warm concoction, each establishment brings distinct creativity to the same base spirit. "We've had a Manhattan, an espresso martini, and now a nice warm mock cider drink," Brady summarizes, still marveling at the variety.

This diversity extends beyond beverages. V2 makes syrups in-house and infuses its own spirits. Courtney recently experimented with homemade limoncello for the group's new restaurant, Mangia, using V2 as her "guinea pig." Hideaway leverages its espresso equipment to create coffee cocktails other bars can't replicate. Roma operates Alesatian Brewery upstairs while serving creative cocktails downstairs.

The Road Ahead

As Janet and Brady wrap up their preview—admittedly feeling the effects of three bourbon drinks—they reflect on the challenge ahead. "We have eight different restaurants participating. We've only hit three," Brady notes with a laugh. "And at this rate, we may not hit more than... we may not hit. This may be the only three that we do."

The bourbon requirement, while creating cohesion, presents its own challenge. "It's great because I love bourbon," Brady admits. "It's not great because when you're trying to drink eight bourbon drinks..." He trails off, closing one eye dramatically.

Despite the research hazards, both hosts express genuine excitement for the competition's potential. The event represents more than just cocktails—it's about community resilience, creative expression, and proving that Old Town thrives year-round.

For those planning to participate, Brady recommends spreading the experience across the full weekend rather than attempting all eight venues in one night. "You have plenty of opportunity to come in and try these drinks at all these different places," he suggests diplomatically.

Raising the Bar

Old Town on the Rocks ultimately celebrates what makes Winchester's downtown special: independent businesses run by passionate people who genuinely care about their craft. Greg's encyclopedic alcohol knowledge, Courtney's nerdy creativity, and Chris's willingness to experiment with warm butter cocktails all reflect a community that refuses to phone it in.

As Janet becomes a newly minted VIP at Hideaway (complete with keychain proof), she embodies the event's spirit—locals discovering new dimensions of familiar places, supporting neighbors, and finding reasons to gather during the coldest, darkest months.

"Just share it on Facebook," Brady urges those who can't attend. "You don't have to come out for Old Town on the Rocks. You can just share it, 'cause people may see it and want to go out."

In the end, that's what community looks like: raising a glass together, even when it's cold outside.

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Old Town on the Rocks takes place January 16-18 throughout Old Town Winchester. Find more information at friendsofoldown.org or search "Friends of Old Town" on Facebook and Instagram.