People drive past the turnoff on Route 220 more than they'd like to admit. Owner Will Barkett hears about it almost daily from customers walking up the stairs at 18 S Roanoke Street: "I've driven by on 220 a thousand times and had no idea this spot was here." He's talking about 1772 Rooftop on Main, the bar sitting on top of the Pie Shoppe, but he could be talking about half of downtown Fincastle. The town looks, from the highway, like a courthouse and a few blocks of brick storefronts. What it actually runs on after 5 p.m. is a handful of small, personality-driven businesses, each keeping its own hours, plus one thing that never closes at all.
That last part matters more than it sounds. Fincastle isn't a downtown grid where you can wander until something looks open. It's small enough that a single business's day off changes what your evening looks like. Knowing the actual rhythm, not just the list of names, is the difference between a good night out and a drive back down 220 for takeout.
One Roof, Two Businesses, Different Clocks
The building at 18 S Roanoke Street does double duty. The Pie Shoppe occupies the ground floor, a family bakery and sandwich counter. Upstairs is 1772 Rooftop on Main, which didn't exist as a concept until the Barkett family reopened the Pie Shoppe in 2019 and, according to WDBJ7's Hometown Eats feature, looked up the following year and decided the roof needed a bar.
What they built is not subtle. The bar itself is the fuselage of a 1948 Beechcraft V-tail Bonanza, purchased and converted by Black Dog Salvage in Roanoke. You're drinking a cocktail inside what used to be an airplane, looking out over the Botetourt County Courthouse and the Blue Ridge Mountains behind it. The name isn't decorative either. Fincastle was chartered in 1772, which makes the town 254 years old this year, and the restaurant took its name directly from that founding date.
The courthouse the rooftop looks down on is worth the view on its own. It holds documents signed by Thomas Jefferson and other Virginia patriots, part of what makes the entire town a listed entry on the National Register of Historic Places.
What's Actually Open, Night by Night
This is where the planning gets specific. The Pie Shoppe posts consistent hours on its own site: closed Monday, 11 a.m. to 5 p.m. Tuesday, 11 a.m. to 9 p.m. Wednesday through Saturday, and 10:30 a.m. to 2:30 p.m. Sunday.
The Rooftop is a different story, and not because the business is unreliable. It's because every directory that lists it seems to have a slightly different version of its schedule. Yelp has it closed Sundays. WDBJ7's own reporting has it open Sunday mornings into early afternoon. A chamber of commerce directory drops Tuesday from the schedule entirely and pushes the opening time to 4 p.m. on the days it does list. None of these are necessarily wrong, since small restaurants adjust seasonally and directories lag behind real life, but it means the smart move locally isn't trusting the first search result. It's calling ahead at 540-632-8099 or checking 1772rooftop.com the day you're actually planning to go.
| Day | Pie Shoppe (downstairs) | 1772 Rooftop (upstairs) |
|---|---|---|
| Monday | Closed | Closed |
| Tuesday | 11 a.m. – 5 p.m. | Varies by source, call ahead |
| Wednesday | 11 a.m. – 9 p.m. | Open, hours vary |
| Thursday | 11 a.m. – 9 p.m. | Open, hours vary |
| Friday | 11 a.m. – 9 p.m. | Open, hours vary |
| Saturday | 11 a.m. – 9 p.m. | Open, hours vary |
| Sunday | 10:30 a.m. – 2:30 p.m. | Varies by source, call ahead |
The one thing every version of the schedule agrees on: Monday is dark for both floors of that building. If you're planning a week around this spot, that's the night to route around, not through.
A Stage That Runs on Its Own Calendar
A mile or so down Roanoke Road, past the point where downtown thins out into open ground, sits Attic Productions, a community theater that has been staging shows since 1995 out of the D. Geraldine Lawson Performing Arts Center. This is not a nightly venue. It runs on production cycles, which means whether there's anything to see on a given night depends entirely on what's currently in rehearsal or run.
This summer's production was Sondheim and Lapine's "Into the Woods," which closed July 26 after a run directed by Kerry Williams, with musical direction by Jessica Mansfield and choreography by Mandy Masching, according to the Fincastle Herald's coverage of the closing week. Before that, the spring slot belonged to "Never After Happily," a farce that ran late April into early May. Shows typically run Thursday and Friday evenings at 7:30 p.m., with Saturday and Sunday matinees at 2:30 p.m., and tickets run $20 for adults and $15 for students. With the summer show closed, whatever's staged next hasn't posted yet. Check atticproductions.info directly before building an evening around it, since the theater only comes alive on the calendar it sets for itself, not on demand.
The distance matters too. This isn't a walk from Main Street the way the Rooftop and the Pie Shoppe are steps from each other. It's a drive, short but real, which means a theater night and a downtown dinner don't happen on the same trip unless you're deliberate about timing them.
The One Thing Open Every Night of the Week
Everything above runs on somebody else's clock. The exception is the town itself. Historic Fincastle, Inc. maintains a self-guided walking tour covering more than 40 structures built in the late 1700s and 1800s, all part of the National Register listing that covers the entire town. You can pick up a paper brochure at the tourism office on East Main Street, or pull up the GPS-enabled version on your phone, which locates you and points out what's nearby without needing an appointment or an open storefront.
The town's history has some specific texture worth knowing if you're walking it after dinner. Fincastle was once home to Judith Hancock, who married the explorer William Clark, tying the town into the Lewis and Clark story in a way most people driving past on 220 wouldn't guess. None of that requires a ticket or a reservation. It's the one part of an evening here that works regardless of what day it is or whose hours you missed.
Putting a Night Together
If you want dinner and a show in the same evening, Thursday is your best bet during an Attic run: the Pie Shoppe and (most likely) the Rooftop are both open, and Thursday is one of the two weeknight performance slots. If a show isn't running, Wednesday through Saturday still covers dinner downtown, with the walking tour filling in before or after depending on daylight. Sunday afternoon works for a slower pace, since the Pie Shoppe closes early and the Rooftop's hours are the least consistent across sources that day. Monday, plan around it entirely. Nothing on Roanoke Street is expecting you.
None of this is complicated once you know it. It's just not obvious from a website or a drive-by glance at the courthouse. That's usually true of small towns worth paying attention to: the good version of a night out here isn't hidden, it's just scheduled a little differently than you'd assume.
If you're the kind of person who likes knowing a town this well before deciding anything else about it, that's exactly the conversation I like having. I'm Alexandra Taylor, and whether you're curious about a specific street in Fincastle or just want a local's read on the towns around Botetourt County, I'm happy to talk it through. Schedule a free consultation whenever you're ready.
