Valentine’s Day might come once a year, but Bend boasts a bounty of delightful date options all year long. To get you in the mood for whichever type tickles your fancy, here are some ideas for your next great date.

A date for wine lovers

While Oregon’s biggest wine regions lie on the rainier side of the state, our high desert wine scene has been exploding. 

Start smart by planning sober transportation beforehand. Uber or taxis fit the bill, or ask a teetotaling pal to play chauffeur.

Sober ride secured, start in the Old Mill District with tasting dates at Va Piano Vineyards and Evoke Winery (formerly Naked Winery). Split a taster tray in each spot, then stroll the Deschutes River for fresh air, birdwatching, and maybe some shopping.

Next, head north to the Box Factory where Stoller Wine Bar, Elixir Wine Group, and Bledsoe Family Winery all have tasting rooms. Grab a meal at one of these stops to pair with your vino, or hit a food cart close by for something different.

Keep heading north to give your body a wine break with a stroll through Bend’s scenic Drake Park. The picturesque foodbridge makes a nice spot for a smoochy selfie before you link hands and amble into Downtown Bend.

Once you’re Downtown, head for the brand new Domaine Serene Wine Lounge. Their entire menu is crafted to pair with their wines, and a shared taster tray lets you sample before settling on a glass or bottle. Many menu items are sharable, so split a salad and some apps to make a light meal, or go for full entrees and swapped bites at a candlelit table. 

Want to stretch out your wine-venture? Newcomer Flights Wine Bar has an excellent selection of wines and food. Since you’re headed that direction, keep going toward Northwest Crossing where longtime wine spot Portello Winecafe offers amazing flights and flatbreads. Cheers!

A date for outdoorsy romantics

February’s the perfect time for a threesome. Er, not that kind. 

Bend’s well-known as a town where you can plan three outdoor adventures in one day, and winter has tons of picks for your trio of fun. 

How about a morning of skiing, followed by lunchtime bike ride and an early evening hike? Maybe a hike/golf/fishing threeway is more your speed, or any combination to get you playing from dusk ‘til dawn.

Get the juices flowing with a quick scan of Visit Bend’s winter fun page. Got it? Make a list of which forms of outdoor fun sound most up your alley.

Grab a map and plan your other outings in close proximity. For instance, fly fishing midges to catch redband trout on the Crooked River pairs well with a Chimney Rock hike. Plenty of gravel bike routes swoop through spots where other adventures lie, so map out your plans to maximize your full day of outdoor play.

Make the most of mealtimes by seeking out on-the-go breakfast options. Pack a picnic with goodies from Newport Avenue Market so you can set up a sweet lunch date in a warming hut on your favorite cross country ski trail. 

The possibilities are endless, assuming your love of outdoor fun matches your love for your adventure-loving snugglebug.

A date for sustainably-minded sweeties

You love Bend as much as you love your Boo, so why not leave it a little better than you found it? (Er, Bend, not your Boo. Please don’t tell your sweetie all the ways you want to fix them).

Begin by swooping in to pick up your date on a tandem bike or another form of eco-friendly transit that won’t burn fossil fuel. You can exchange homemade cards created with magazine photos or other recycled materials. Prefer to step up your gift game? Shop local at your favorite Bend retailer and avoid all that shipping material (not to mention supply chain shortages). Bonus: You’re spreading love to Bend’s family-owned shops.

When mealtime rolls around, skip the restaurant date and volunteer at Family Kitchen helping those less fortunate. If you do dine out, spread love by being extra kind to your server, bartender, barista, or the grocery store attendant who’s bagging up groceries for your made-from-scratch meal.

If your Bend date includes outdoor play, take a trash bag along to pick up litter on the trail. Tote matching Hydro Flask water bottles instead of throwaway ones, and be sure to pack out all your picnic goodies. 

A stargazer’s ultimate date night

If you and your lovebug have stars in your eyes, listen up! This year, there’s a two-week conjunction of Mars and Venus that kicks off Valentine’s week when the planets will appear within one degree of each other. How Valentiney is that?

Find yourself a spot outside the city limits where light pollution won’t inhibit your dazzling view of the stars. The Oregon Badlands Wilderness or the Scenic River section of the Crooked River Canyon should do the trick. If you’d rather leave the driving to someone else, book a moonlight snowshoe adventure with Wanderlust Tours. They’ll provide all the gear and an awesome naturalist guide, plus snacks and drinks. Pro-tip: They’ve had more than one proposal happen on these adventures over the years, so get that ring ready if you plan to pop the question.

You could also stick close to town with a Bend Ale Trail stop and Worthy Brewing. Grab dinner and a beer, then head for your appointment in the Hopservatory to gaze at the heavens through their powerful telescope.

A posh date for luxe loving honeys

Sometimes you want something swanky. Bend can deliver!

Start with a spa date for two at one of Bend’s luxurious day spas. Get tandem facials or a couples’ massage to begin your day of bliss in style.

Next, some shopping. Head for the Old Mill District and slip in some of that aforementioned wine tasting between shopping stops at local retailers like Vanilla Urban Threads, Savory Spice, Kara’s Kitchenware, and Hello Sunshine. 

Lunchtime? Grab a river view table at Greg’s Grill, or start happy hour with drinks at Rapa Nui Tiki Bar.

If Downtown Bend is more your scene, enjoy a romantic stroll in Drake Park with coffee in hand from Bellatazza. Bonus: You’re steps from several fabulous jewelry shops if a little sparkle sounds like your sort of souvenir. 

Pre-dinner drinks at San Simon will start things off right, and a tasty steak dinner at Bos Taurus will set the mood for your evening of romance. Bon appetit!