Clarksville, founded in 1871 by freedman Charles Clark as a settlement for former African-American slaves in the aftermath of the Civil War, couldn’t hold onto every part of its history.

Despite the neighborhood’s roots, its demographics shifted heavily in the early 1900s as land values increased alongside city-enforced segregation. The neighborhood now occupies Austin’s second most expensive zip code, with home prices currently averaging $462 per square foot.

If North Loop serves as a living history museum for Austin’s dwindling class of working weird, Clarksville represents the influence of its gentry, peppering the city’s usual assortment of craftsman-style homes with historic Victorian specimens and picture-perfect bungalows.

There’s also a castle, if that’s your thing — originally built as a military academy, sure, but still doing plenty of favors for the district’s general air of nobility. A big turret has a way of doing that.

Even as the downtown core only minutes away hopped a runaway train to vertical density, Clarksville more or less maintains itself as the an independent enclave of single-family homes, capable of sustaining its lucky few residents without forcing them to venture beyond its borders any more than absolutely necessary.

This makes Clarksville prime territory for an Austin staycation, even if you’re only pretending to live there for 36 hours.

Before we begin, let’s set some terms. Despite the popular understanding of even the most native Austinites, most don’t realize the area commonly known as Clarksville is a lot larger than the actual Clarksville Historic District. Here’s a map from the Clarksville Community Development Corporation versus what Google and other neighborhood maps commonly designate as Clarksville:

Folks get a little picky about this distinction, so let’s make it clear that we’re talking about spending time in the larger region commonly known as Clarksville. There’s not nearly as much to do if you limit yourself to the historic district, unless you’re here just to look at homes and wish you owned one here.

Friday

5:00 p.m. – Happy Hour Heist

Jeffrey’s, a fine dining institution in a neighborhood hosting a few more than its fair share, first came on the scene in 1975, but its acquisition and renewal six years ago by local hospitality group McGuire Moorman, along with the opening of next-door spinoff Josephine House, put the restaurant back on the map after years of flagging business and popularity.

Although there’s nothing remotely the matter with the 42-ounce porterhouses ($165) dropping jaws in the dining room, for my money, the best way to dip your toe into this Clarksville icon is via its daily happy hour. From 4:30 to 6:30 p.m, Tuesday to Sunday (and all night Monday!), you’ll find a half-priced bar menu and $2 discounts on every cocktail, beer, and wine in the house.

That bar menu, by the way, crushes plenty of full-sized menus at other upscale joints in the city, with a dry-aged wagyu burger and fries clocking in at a mere $12 during happy hour. It’s not dive cheap, but it still feels like you’re getting away with something.

7 p.m. – But Wait, There’s More!

If you stick to the lighter side of happy hour, you might still have Clarksville’s local restaurant scene on the brain — and if so, all you’ve got to do is walk across the street from Jeffrey’s. Cipollina first opened in 1999 with a menu all over the map, feeling Italian at heart but also integrating French and Mediterranean influences into a self-proclaimed unstuffy, neighborhood bistro experience.

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But hitting three targets is tough, so by 2014, the restaurant recalculated to focus exclusively on Italian cuisine, and I don’t think anyone’s looked back since. Wood-fired pizzas ($10 – $18) topped with a spectrum of wonders from sweet onion compote to prosciutto are a local favorite, and the dinner menu’s assortment of dishes backed by the restaurant’s fresh homemade pasta ($15 – $26) will change your life if you’ve never ventured out of the box.

Sharing the building with Cipollina is Fresh Plus Grocery, one of the engines driving Clarksville’s self-sufficiency. It’s a full-sized grocery store that’s operated in the neighborhood since the 1920s, and once you’ve visited, you’ll wonder why every Austin neighborhood isn’t as lucky.

It’s a great spot for grabbing a sixer after dinner, or just grabbing dinner, with a thoughtful selection of items taking you way beyond a normal neighborhood bodega. Wouldn’t it be nice if they built one of these downtown?

9 p.m. – Neighborhood Character

Clarksville, probably owing to its status, lacks bars — yes, there are great bars at many of its restaurants, but you know what I’m talking about.  If you’re looking for a dedicated late-night solution, you might be forced to venture one block south of West Sixth Street, Clarksville’s southern boundary, to dives like the Mean-Eyed Cat and Donn’s Depot. But we’re following rules here, and folks in Clarksville enjoy an early bedtime.

That reminds me, another thing you won’t find in the neighborhood: hotels. But you’re not going to mind if you book something like this furnished guest house, one of the best hidden gem rentals I’ve found in the city. There’s also plenty to choose from on Airbnb, as long as you book a few weeks in advance.

Saturday

10 a.m. – Counterpoint

Although Counter Cafe opens at 7 a.m. every day, you might not feel inclined to roll up then — it’s a vacation, after all. Of course, considering the seating situation in this microscopic ode to the classic American diner, you’d be wise to show up as early as possible to ensure a shorter wait for one of what appears to be about 10 tables.

And it’s really worth it, with an easy menu of diner favorites jazzed up with words like “organic” and “local.” A crab cake Benedict with homemade hollandaise ($15) is both excellent and about as high-end as things get around here, but you’ll also never go wrong with eggs any style, served with a fresh biscuit, bacon, or sausage ($9). 

11 a.m. – The Boutique Shuffle

The shopping scene in Clarksville will keep you pleasantly occupied, if you like that sort of thing. Though its location has changed a few times since it opened in 1970, Clarksville’s Whole Earth Provision Co., just a few blocks down North Lamar Boulevard from Counter Cafe, might be the best link to old Austin on this side of the neighborhood. Its selection of clothing, camping equipment, footwear, jewelry, and more is planet-conscious and often local or fair trade. There’s plenty of weirdness to be found here in a city with a dwindling supply, and you might find yourself seriously considering picking up a hammock after a test drive. Is there a time limit?

Once you’ve had your fill of the sandals set, check out a slightly different kind of weird at Fortney’s on West Sixth Street, a furniture store out of your strangest dreams ever. Billed as supplying “eclectic home furnishings,” Fortney’s is a treasure trove of statues, wall art, antique flags, and every other off-kilter furnishing and decor solution you’d expect from a store proudly billing itself as “The Most Austin Store in Austin.” Last time I checked their site, they were selling a phone booth.

1 p.m. – Under the C

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The aptly-named Clark’s Oyster Bar is owned by the same folks behind Jeffrey’s — their hold on the Clarksville market is pretty well-cinched at this point. If you’re a fan of the briny deep (or a good hamburger), it’s one of the nicer lunch options in the area.

I’m not saying you’re required to dive into the extensive caviar list (with options ranging from $30 – $240) or the cold bar selections of raw oysters (most are $3.50 each), but the red snapper ceviche ($19) sounds better and better as the outside temperature rises past insanity. Grilled shrimp toast ($16) is a highlight, a sort of austere cousin to the excellent lobster roll ($34). 

2 p.m. – Artsville

Get a little culture running through your veins at Artworks, a showroom just down West Sixth Street from Clark’s, with works of paint and sculpture by local artists on display and for sale. You might not feel like carting around a painting all afternoon, but give it a look anyway and see if something grabs you. What’s a vacation without art?

4 p.m. – Record Time

If you’re from here, Waterloo Records is old news, but the excitement of digging through vinyls and band shirts hasn’t changed much since the store opened in 1982, though it’s moved to a larger space since then. The notion of a physical store for music is less and less of a thing, so respect the classics and pay the place a visit. You’ll never find some of this stuff on iTunes.

6 p.m. – Are You Experienced?

Picture your next dinner party at Cafe Josie. No one goes home hungry with The Experience. (Read: All-you-can-eat) https://t.co/1uyMLhomXF pic.twitter.com/sEXRazZco0

— Cafe Josie (@CafeJosie) July 27, 2017

Cafe Josie, a neighborhood farm-to-table spot fashioned from a former Clarksville carriage house in 1997, offers one of the better dinner…experiences in the city.

“The Experience,” the cafe’s signature all-you-can-eat chef’s tasting ($45 per person), allows diners to choose from 16 tasting menu items — as many as you want, as many times as you want. It’s a revolutionary deal for large groups, but two people will enjoy the menu’s range from grilled okra and peach salad all the way to fried oysters and smoked brisket. It’s really something, man.

9 p.m. – Some Things Never Change

Again, if you’re from Austin, Amy’s Ice Creams practically blends into the city’s background. But much like Waterloo Records, that raises a question — how long has it been since you actually went there? It’s probably been too long, and Amy’s still does it right more than 30 years after the grand opening.

Prices and flavors change with the wind, but you’ll still get a homemade waffle cone here for roughly $5.00, and the scooping flair comes free. Go for their boozy flavors, if they’re available — Shiner beer and whiskey caramel are past favorites.

Sunday

10 a.m. – Soda Jerks

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Your last meal in Clarksville could also be its most historical, at Nau’s Enfield Drug, a full-service pharmacy, old-school soda fountain, and lunch counter dating back to 1951. Every pharmacy used to operate something like this, with burgers and malts cozied up next to headache powder and cough drops, but it’s harder and harder to find in the modern era of drive-thru drugstores and national chains.

The breakfast at Nau’s is a dirt-cheap throwback to that bygone era, with no-nonsense breakfast plates and huevos rancheros clocking in at around $7.00, and big, fresh breakfast tacos starting at $2.50 apiece. You’ll only need two, since there’s a good chance you won’t leave the place without trying a chocolate ice cream soda ($4.95). It’s just the right thing to do.

11 a.m. – Paint the Town

You’ve probably passed it a few times by now if you’re bumming around the neighborhood, but the HOPE Outdoor Gallery deserves a closer look. This graffiti gallery — or “community paint park” — was reclaimed from a hillside condo development abandoned in the early stages of construction, now hosting constantly-changing street art and the city’s most consistent Instagram popularity.

But Austin’s still Austin, so the site won’t stay this way for long, with relocation plans already on the horizon. Even in a historic neighborhood like Clarksville, nothing lasts forever.

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