One Delicious Day in Joseph

This tiny Eastern Oregon town has big things going on—big views, big history, big plans, and big-hearted locals. Just the first glimpse of downtown will stop you in your tracks, it’s hard to believe that the majestic Wallowa Mountains towering in the background are real, and after a few days spent exploring the miles upon miles of unspoiled prairieland, spectacularly scenic tapestry of Eagle Cap Wilderness trails, and charming array of restaurants, shops, museums, and galleries, don’t be surprised if you end up booking your next trip before you’ve even left.

Regardless of whether you hole up in The Jennings Hotel the entire time (understandable), or hike a different high lake every day, it won’t take long to understand how this wee but lively Wallowa County town has made a name for itself as a bona fide destination for adventurers both artistic and extreme.


Map * Weather Check * Local News


The most direct route from Portland to Joseph is via Highway 84. Most notably, you pass through Hood River, The Dalles, Pendleton, and La Grande, before veering off onto Highway 82 and passing through a string of small towns like Lostine, Wallowa and Enterprise. From Enterprise, it’s a five minute drive onward to Joseph.


Some travelers are pedal to the metal, some love a good pit stop. As a meandering member of group B, I’m happy to share a few of my favorite snacking, sipping, and souvenir stops en route to Joseph.

Troutdale: Sugarpine Drive-In (soft serve, sundaes, salads, sandwiches)

Hood River: Broder Øst (Scandinavian brunch fare)

Bingen + White Salmon: The Society Hotel Bingen’s cafe (coffee, pastries, salads, sandwiches) + White Salmon Baking Company (wood-fired bread and pastries, Monday is pizza night, FYI)

The Dalles: Sunshine Mill Winery (top contender for most unique tasting room ever), Baldwin Saloon (food’s okay, ambiance is excellent)

Pendleton: Pendleton Mill and Store (buy a picnic blanket, take a factory tour; info here)

La Grande: Side A Brewing (internationally-influenced pub grub); Wine Down (wine, salads flatbread)

Enterprise: Terminal Gravity Brewing (stuff your face); Wild Carrot Herbals (moisturize your face); 6 Ranch beef’s Liza Jane’s Farmstand (local honey, meat, and produce, cash payment’s on the honor system)

Side Note: I also love the drive from Bend to Joseph via the Painted Hills; the 7-hour trek isn’t for the faint of heart or sore of butt, but it’s an incredibly scenic, solitary sojourn through some of Oregon’s most beautiful country. Get a pint of Painted Hills Pilsner at Tiger Town Brewing Company in Mitchell, a wedge of strawberry rhubarb pie à la mode at Dayville Cafe, and in Baker City, grab huevos rancheros at busy Lone Pine Cafe and a brown butter Rice Krispie treat for the road at Sweet Wife Baking.


A superbly stylish passion project dreamed up by “accidental hotelier” Greg Hennes and brought to life by an ambitious Kickstarter campaign, The Jennings Hotel is an unlikely mecca of art, design, and creative camaraderie right in the heart of downtown Joseph, on the top floor of the historic Jennings Building, a two-story circa-1910 brick structure that could have been pulled straight from a spaghetti western.

Inside, things get decidedly more modern; each room was designed by a different acclaimed artist, architect, or designer, and no two are the same—the bed in Room 3b is wrapped in a handmade quilt by Portland’s Moonshadow Goods, while Room 6’s geometric wall mural was designed by the Shelter Collective in Asheville, North Carolina. Some rooms have private bathrooms, others share, and everyone’s welcome in the Scandinavian-style cedar sauna, where detailed instructions on how to properly löyly await.

Across the hall, the communal kitchen and living room inspire conversation over a shared meal or bottle of wine as Cat Stevens plays on the turntable, while the floor-to-ceiling wall library sends Dostoevsky and Dahl-laden bookworms scurrying for a seat by the wood-fired stove. Downstairs, find cold cocktails and hot, bubbling wood-fired pizzas at The Gold Room, run by two talented Ava Gene’s alums, and the perfectly-curated Small County boutique, curated by Hennes and his partner, interior designer Ashley Tackett.

After a night of deep, restful sleep the likes of which is only possible in a town with no stoplights and near-zero light interference, wake up, grab a cup of Stumptown Coffee and something sweet from Arrowhead Chocolates shop down the street, or a hearty cowboy-style breakfast a few steps away at Old Town Cafe, then decide what the day’s adventures will hold—a twenty-mile trail, a downtown walkabout, or perhaps just breakfast and books in bed. (Edited from my original writeup in 1859 Magazine)

Side Note: My favorite room? Number 2, a gorgeous, spacious corner suite with a stylish living area, extra twin bed, views of the Wallows, door directly out to the shared terrace overlooking Main Street (and, surprise, the Wallowas), and prime location right across the hall from the sauna.


*Cold weather coat, gloves, hat

*Swimsuit (if planning on Wallowa Lake laps or sauna time at The Jennings Hotel)

*Picnic provisions (I’m a food control freak, and shopping spots are scarce here, so if you’re super specific about what sorts of cheese and chocolate you like to eat, consider bringing a cooler with enough picnic provisions to last you a few days)
*Backpack, water bottle, and sturdy shoes (for hiking)


From Terminal Gravity Brewing’s open mic night to one-man plays about Walt Whitman at the Josephy Center for Arts and Culture, there’s a lot going on in Eastern Oregon, here’s the Wallowa County Chamber of Commerce calendar.


*Learn traditional skills like spoon carving, canning, and hat-making at the Prairie Mountain Folk School

*Catch a show at the OK Theatre in Enterprise

*Show your stuff at Terminal Gravity brewery’s Open Mic Night


JUNE: The Wallowa Mountain Cruise Car Show takes over Joseph’s main street

JULY: Pack your best boots for July’s famous Chief Joseph Days Rodeo

AUGUST: 4-H, wool competitions, and Bessie Bingo; the Wallowa County Fair has it all


8AM: Cowboy Coffeetime

Saddle up and ride over to Red Horse Coffee Traders—quite honestly, we’re never sure if this shop’s going to be open or not when we go, but if it is, it’s a cozy and charming glimpse of local life, with a side of organic house-roasted coffee, fresh-baked cheddar chive scones, and homemade quiche.

9AM: Big Ol’ Breakfast at Old Town Cafe

Corn cakes and fried eggs, Yukon Gold potato home fries, and cinnamon rolls the size of a steer’s hoof—Old Town Cafe is where you want to be when your internal breakfast bell tolls.


10AM: Local History Lesson  

Visit the bronze statue of Chief Joseph on Main Street, then visit the impeccably-arranged volunteer-run Wallowa County Museum. There’s a lot of deep, dark, and sobering Native American history here, and as you make your way around the region, you’ll have a much greater understanding of what was taken from Chief Joseph and the Nez Perce tribe.

11AM: Stroll the Streets

Stock up on essential oils and handcrafted soaps at BeeCrowBee, interesting books and baubles at Copper Creek Mercantile, something fun for Fido at The Dog Spot, Good Food Award-winning huckleberry and Stumptown espresso truffles at Arrowhead Chocolates, and carefully curated handcrafted artisan goods and artwork at Small County—located on the ground floor of The Jennings Hotel, this exquisite shop, self-described as “one part general store & one part art gallery & one part bottle shop,”  is curated and run by hotel owner Greg Hennes and his partner, interior designer Ashley Tackett. And since it’s whiskey o’clock somewhere, stop into Stein Distillery for the Wallowa Whiskey Flight or a Whiskey Mule mini-cocktail; call ahead to arrange a distillery tour.


12PM: Pretty Picnicking

Pack up your picnic provisions or buy them at the Small County shop in The Jennings Hotel (there’s also a well-stocked local market on the main street, and you never know what delicious seasonal surprises you’ll find at the aforementioned Liza Jane’s Farmstand), then hit the road.

Next stop, one of these incredibly scenic local hotspots.

*Swim, SUP, fish, float your boat, and more at Wallowa Lake State Park, which has a hefty 200+ site campground that looks like a throwback from your childhood family camp trip days come summertime—roaming packs of wild kiddos, mini golf course, the smell of s’mores in the air. For a fun dose of nostalgia, pop into the historic Wallowa Lake Lodge for a marionberry syrup-soaked Eagle Cap Giant German Pancake breakfast, or just a peek around the lovely old lobby.


*Hike into the breathtaking Eagle Cap Wilderness, where this wondrous web of trails will take you along the Wallowa River, lead you to one of the high lakes, weave past rushing waterfalls, and offer up the sort of breathtaking natural splendor that makes you incredibly glad to be an Oregonian, permanent or temporary.

*Feel extremely insignificant (in a good way) at the Hat Point Lookout.

*Drive the 10-mile Zumwalt Prairie Preserve loop, stopping to hike one or all four of the preserve’s terrifically-scenic trailheads. This stunning swath of land is the largest intact grassland in all of North America, and its beauty and serenity will haunt you forever. (I mean, unless you’re soulless.) Google Maps can get kvetchy out there, so save or print The Nature Conservancy Zumwalt Prairie Preserve guide before you go.


Side Note: Speaking as someone who had to (watch her brother) change a flat tire in the gravel parking lot of the Imnaha Store and Tavern post-Zumwalt Prairie Preserve loop, check your spare before you go! And maybe bookmark a tire-changing YouTube tutorial, if you don’t have your very handy little brother on board. Wear sturdy shoes and take plenty of water, snacks, a first aid kit, a blanket, and a set of warm clothes just in case.

7PM: Pizza and Pinot? Yes, Please.  

After all that driving, hiking, and jaw-dropping at the incredible views, you’re no doubt hungry enough to eat one of the beautiful life-size bronze statues Joseph’s main street is known for, so head to The Gold Room for rustic charm, crackerjack cocktails, and gorgeous salads, pastas, and wood-fired pizzas. Nesting underneath The Jennings Hotel, the restaurant is run by young and talented chef-owners (and alums of Portland’s acclaimed Ava Gene’s) Ross Effinger and JoMarie Pitino, who were lured east by the wild Wallowa County beauty and downtown Joseph’s easy charm. Plunk down at the bar and sip Willamette Valley pinot noir with your roasted local beets with buttermilk coriander dip, locally-sourced 6 Ranch grass-fed beef meatballs atop rich, creamy heirloom polenta, and piping hot, beautifully-blistered wood-fired caramelized onion, caciocavallo, and Calabrian chili pizza. If it hasn’t sold out, buy a loaf of JoMarie’s bread to go.


If The Gold Room isn’t open, or you’ve eaten there four nights in a row and want to mix things up, get tasty homemade Mexican food at La Laguna Mexican Restaurant, or creative internationally-influenced tapas and homemade cheesecake at The Dog Spot, part cafe, part pet boutique (I know, not the most likely combination, but it works). For a Bavarian-style supper in a charmingly old-fashioned family-run restaurant, drive the 10 minutes over to Wallowa Lake to Vali’s Alpine Restaurant (dinner reservations often required, and if you’re in town on a summer weekend, pre-order or line up early for their sell-out weekend morning doughnuts).

If you’re staying at The Jennings Hotel, there’s a beautiful, fully-stocked shared kitchen with an oven, electric range, and all necessary cooking utensils and dishware, so bring your own ingredients and whip up a delicious meal, then eat at the communal table or outside on the veranda, overlooking the Wallowas.


9PM: Nightcap

LIsten to live music at Embers Brewhouse, which lays claim to the “largest selection of microbrews in Eastern Oregon,” or play pool with the locals at the Rusty Spur Bar and Grill (free on Sundays).

After that, it’s time to stargaze and snuggle. You’ve had quite a day!

And that’s a wrap! If I’m missing something that’s unmissable, drop me a note at, or message me on Instagram at @jenlikestoeat