Centrally located in Bend, the Old Mill District is the perfect spot to take a load off after a full day of adventuring (or after a particularly long work week, or on a random Tuesday for no reason at all.)

At some point during the day in Bend all the hiking, biking, paddling, skiing, golfing, climbing, snowboarding, snowshoeing, birding, camping, fishing, shopping, floating, river surfing, running, etc. comes to an end. But here’s the best part: That’s when the relaxing begins. And what better way to relax than Happy Hour in the Old Mill District?

There’s nothing more welcoming than Greg’s Grill on the Deschutes where Happy Hour is every hour! That’s right, enjoy special food and drink prices all day long at one of the district’s original restaurants. Have a seat at the bar or in the lounge and choose from $6 well drinks and select wines. The Happy Hour food menu includes sesame seared tuna, baked brie and more. The ribeye sliders come with red onion and blue cheese and pair perfectly with a $4 draft Rainier beer and a game on one of the three huge TVs behind the bar. On Tuesday nights, enjoy live music at Greg’s Grill from 6 to 8 pm. Greg’s is also the premier spot to take in one of the 50 or so shows each summer across the river at Hayden Homes Amphitheater. Patio seating is available first-come, first-served, additional “concert fee” may be added to your bill so check in with your server first.

Two gals enjoying wine and food on the outside patio along the Deschutes River at Greg's Grill in the Old Mill District

Looking to get exotic on your visit to Bend? Rapa Nui Tiki Lounge will transport you to an indoor Pacific paradise where you can indulge in unique concoctions like the Viking Fog Cutter, Sidewinder’s Fang or traditional favorites like a Mai Tai or Blue Hawaiian. Coming with a group? Dive into a shareable Scorpion Bowl or Chilled Monkey Brains.

Lady Bird Cultural Society offers an upscale option that harkens a dinner and drinks experience from days gone by. They offer varying Happy Hour specials on their Prohibition-era cocktails during the summer months and feature a unique menu that includes charred octopus, wood roasted aged duck, and cast iron sea scallops. Lady Bird’s fun mocktail menu is worth a try as well. The “Fins Up” features zero proof mezcal, pineapple, coconut and luxardo cherry. A “not-too-sweet” treat for sure.

Four friends cheersing four different cocktails at Lady Bird Cultural Society in Bend, Oregon

Speaking of summer, find the perfect end to your Bend adventures with a margarita from Hola! Nouveau Mexican-Peruvian Cuisine (pictured above). For years, Hola! has been a local’s favorite with its Peruvian and Mexican-inspired menu and the kind of finely crafted margs and mojitos you’ll be telling friends about. Happy Hour happens Monday-Friday from 3 to 5 pm and you’ll find $4 beers, $3 off all appetizers, including nachos, Portobello quesadillas and ceviche Mexicano.

Anthony’s at The Old Mill District is Pacific Northwest dining to the core, with fresh seafood and local produce, wines, beers and more. Anthony’s has an extensive Happy Hour menu available from 3 to 5:30 pm and includes $7 draft beers from Bend’s Deschutes, Goodlife and Van Henion breweries. You’ll find $7.50 glasses of wine, and $8.50 specialty cocktails like a Moscow Mule or Aperol Spritz. The Happy Hour menu also includes Anthony’s award-winning clam chowder, crab-stuffed mushrooms, Hawaiian ahi poke, Northwest Manila clams and more.

Two friends enjoying wine on the patio in front of Va Piano Vineyards in the Old Mill District in Bend, OR

For the wine lovers Va Piano Vineyards Wine & Champagne Bar in the Old Mill District offers a “locals” deal on Mondays: $2 off glasses of wine or bubbles. The Walla Walla-based winery’s tasting room is a relaxing spot to unwind with a flight of delicious varieties and you can catch live local music on Wednesday nights during the colder months.

Of course, beyond the Old Mill District, you’ll find fun Happy Hours or Locals Night deals all over Bend at some of our favorite places like Deschutes Brewery, Silver Moon Brewing, and 10 Barrel Brewing among others.

Content curated by Ted Taylor