The Old Mill District in Bend, Oregon makes date night easy.  Whether you’re an art aficionado, nature lover or foodie, there’s something for every couple to enjoy together.

A Riverside Stroll: I have no doubt marriage proposals have happened along the wild and scenic Deschutes River as it winds through the Old Mill District. It’s just that beautiful of a setting. The Deschutes River Trail – Old Mill District is a paved path that runs about 3 miles on both sides of the river. Three footbridges over the river connect the trail and it’s perfect for a leisurely walk before Happy Hour (margaritas at Hola! anyone?) and dinner or to kill some time before catching a movie or concert. In the summer, you’ll be entertained by the river floaters, kayakers and surfers. And year-round you’re likely to see a wide array of wildlife.

Reward yourself for the “strenuous” walk along the river with a visit to the Ben & Jerry’s scoop shop for a cone or shake.

A Couple Who Cooks Together….Has fun together! Spice up your relationship with a unique evening learning a new skill or discovering a new dish with Kara’s Kitchenware’s cooking classes. Future classes include Vegan Italian, French classics and a taste of the Middle East. The classes run from 6 to 8 pm.

Art Gallery Tour: Natural beauty abounds around the Old Mill District, but within the shops and restaurants lies an art scene that’s just as attractive. The district’s newest piece, “Bountiful” honors the Old Mill’s founder, Bill Smith and depicts a larger-than-life Osprey in flight. You can find it in front of Cafe Yumm in one of the district’s ponds. Peruse the Old Mill District’s Tin Pan Alley collection, the dragon mural from Japanese artist Yuga Negishi and the “You Stole My Name” collection from Sisters painter/storyteller/musician Dennis McGregor.

What’s more, you can pop in and meet the makers at the Lubbesmeyer Art Studio & Gallery, Tumalo Art Co., The Stacks Art Studio & Gallery and Amejko Artistry in the little red shed. The artists are eager to share stories about their creations and offer design ideas for your home. And no date night is complete without the obligatory selfie in front of the giant “Welcome to Bend” mural outside of Gap.

A couple kayaking on the Deschutes River as sunset in the Old Mill District in Bend, OR

Sunset Kayaking: A few years ago my wife texted me from a garage sale: “I’m buying you a kayak.” Already an avid kayaker herself, she knew I’d quickly take to the magical experience of floating along the Deschutes River or on one of the numerous and breathtaking high-mountain lakes nearby. And I’m proof you don’t have to be an expert kayaker to find true joy, peace and tranquility out on the water. That experience awaits you in the Old Mill District. You can rent kayaks or stand-up paddle boards from Tumalo Creek Kayak & Canoe and head straight for the river right out their back door. Enjoy a sunset paddle after dinner or spend a weekend afternoon on the water enjoying the scenery.

Wine Tasting: Sometimes a perfect date night is simply a quiet conversation over a nice glass of wine. Evoke Winery is a Hood River-based winery with a tasting room and patio just steps from the Hayden Homes Amphitheater. Whether you’re into big reds, dry whites, sweets or all of the above, they have a wine for that. Pop a bottle with your partner and don’t forget to read the back of the label! The tasting room also offers charcuterie and small bites as well so you can make a night of it.

At Va Piano Vineyards Wine and Champaign Bar, enjoy a flight of four 2 oz. pours for just $20. Va Piano’s wines come from premier Washington state growers, including their own Walla Walla Valley Estate Vineyards. If the conversation leads to dinner, Mio Sushi is a perfect option to keep the evening going.

A couple sitting in the sun outside Va Piano Vineyards in the Old Mill District with the sun glowing on their faces.

Live Music: The Old Mill District’s Hayden Homes Amphitheater is the epicenter for live music in Central Oregon. This summer, big time artists Dave Matthews Band, the Beach Boys, Vampire Weekend, Third Eye Blind, Mt. Joy and more hit the stage as part of the Les Schwab Tires Concert Series. The perfect date night starts with a bike ride to the venue where you can park right next to the front gate. And there’s no need to grab dinner beforehand because there are numerous food options to choose from inside: local favorites like Dump City Dumplings, Island Noodles, ZydeGO, Grab and Go, Ben & Jerry’s are just a few of the culinary delights that await. And, of course you’ll find a huge selection of local beers, wines and ciders.

Looking for something a little more intimate? You and your partner can catch local live music every Tuesday night at Greg’s Grill from 6 to 8 pm. Their Happy Hour is every hour and you’ll find some filling dishes and discounted drinks on their special lounge menu.

A couple embracing during a show at Hayden Homes Amphitheater in Bend, Oregon.

Dinner and a Movie; Elevated: The Old Mill District has the standard date-night covered. Play it casual and hit up Pastini after your day of Bend adventures. Enjoy all your favorite Italian dishes (many are offered gluten-free) with a view of the Deschutes River. Get gussied up a bit and visit Lady Bird Cultural Society for an upscale start to the night. They have a diverse prohibition-era cocktail and mocktail menu and their unique dinner menu includes dishes such as octopus and duck in a classy setting. Or, for a little more “Classic Bend” experience, visit the new Mill Works Pub for fresh take on burgers, salads, sandwiches and more. Locals flock to Kona Mix Plate for large-portion Hawaiian dishes and if your night out includes kids, Red Robin is always a favorite. Wrap up date night with a blockbuster movie at Regal Old Mill ScreenX & IMAX, which features an IMAX screen and fun menu that includes all your favorite movie snacks, beer, wine and cider.

Content curated by Ted Taylor