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11 Winter Date Night Ideas in Bend, Oregon

  |  Central Oregon, Happenings, Local Happenings

In a city as vibrant as Bend, there is no shortage of activities for your next date night adventure — even during the winter. On a cloudy day or after a fresh dusting of snow, these date night ideas in Bend are sure to keep you cozy, warm and full of excellent local coffee or craft beer.

Explore the many things to do as a couple in Bend, whether you want to embark on a snowshoeing adventure under the stars or your idea of “adventure” is sampling a new wine.


1. Visit a Historic Hotel With a Brewery, Movie Theater + More

Constructed in 1936 in the heart of downtown, the McMenamins Old St. Francis School was transformed from a Catholic schoolhouse in 2004 to a hotel, complete with classrooms-turned-lodging rooms, a pub, a brewery, a movie theater, event space, and more. Plus, a recent renovation in 2016 added two new buildings with additional guest rooms and a new hidden bar!

The intimate Fireside Bar is the perfect place to grab a drink or a light snack (or a whole meal, if you’d prefer!). You can indulge in a hearty dinner at the Old St. Francis Pub or O’Kanes, or you can eat while you watch a movie at the Old St. Francis School Theater Pub. Don’t miss the stunning soaking pool on site, which is free for hotel guests and just $5 for the general public (but don’t forget to bring your ID, as it is for those over the age of 18). After your relaxing soak, seek out the secretive Broom Closet Bar, a speakeasy of sorts offering classic cocktails with an emphasis on whiskey, scotch and Port. Turn your date night into a mini “staycation” by spending the night at this historic, charming and action-packed hotel in the heart of Bend!


2. Snowshoe to a Cozy Bonfire

Wanderlust Tours Bonfire on the Snow Bend, OR

Photo Courtesy of Wanderlust Tours

Experience a quintessential Bend date night adventure with Wanderlust Tours! Their unique Bonfire On the Snow tour includes a nighttime snowshoeing trip with a guide to a quiet spot in the snowy forest with a glowing bonfire. After traveling through the peaceful snow, relax around the fire with delectable desserts and hot drinks while naturalist guides share fun facts about the forest, its wildlife, and the night sky! Tours depart on select nights through the winter from the Wanderlust Tours office at 7 p.m. This unique tour costs $95 per person, and waterproof boots, pants and jackets are available for rental.


3. See a Show in a Historic Theatre

The Tower Theatre Bend, OR

Photo Courtesy of Dogleg Studios via the Tower Theatre

Whether you prefer comedy shows, artistic films or intimate concerts, the Tower Theatre is your go-to source for entertainment! This nonprofit believes the performing arts strengthen our community and improve our lifestyle. And we couldn’t agree more! Take a look at their upcoming events and get two tickets for a show that catches your attention. Visiting this historic theater means you can support the arts while seeing an inspiring performance or film.


4. Capture the Beauty of Central Oregon After Taking a Photography Class

Bend Photo Tours Night Sky Tour Bend, OR

We are immersed in such spectacular scenery in Central Oregon. It is only right to adequately capture the natural beauty of the area! Embark on a photography adventure with Bend Photo Tours. Grab your camera and explore the area with one of their local guides. Some of their most popular itineraries include Bend Street Photography, The Cascades, The McKenzie, The Night Sky, and Sunrise & Sunset Photo Tours. The two-hour Bend Street Photography tour is an opportunity to photograph the historic heart of Bend, the downtown area, and areas along Mirror Pond where nature meets city life. Learn and practice the basics of street photography guided by an expert local photographer. Or get immersed in nature with a three-hour Night Sky Tour where you will capture stunning nighttime photographs of the stars and serene night scenes. A local photographer will guide you to the best locations and help with proper camera settings for capturing magical images of the expansive night sky!


5. Sample Local Brews

Bend Ale Trail Bend, OR

Bend is a renowned craft beer hub. In fact, the city is deemed “Beer City USA” and has the highest micro-brewery per capita in the nation. So it is only right to experience the best of the city’s brews on your next date night adventure!

Travel along the Bend Ale Trail, the largest beer trail in the west. Simply acquire a passport and receive stamps at each of the breweries along the way. No purchase is necessary at each of the stops, but it’s a great opportunity to sample a variety of Bend beers.

However, it’s not wise to attempt the entire trail in one day! Visit one or two for a more laid-back experience and make it a goal to check off as many as you can throughout the year. This simply means more beer-centric date nights in your future! If you collect 10 stamps, you can stop by or send your completed passport to the Bend Visitor Center to receive your special souvenir, a commemorative Bend Silipint!


6. Solve a Mystery

Bend Escape Room Bend, OR

Work together as a team to solve a mystery at Bend Escape Room. At this physical adventure game, participants are placed in a room and must use teamwork along with elements of the room to solve a series of puzzles and escape the room within a set time limit. Each room has a special theme and unique storyline. Pick from the various room themes, including R.E.S.C.U.E., Crimson Storm, Knight & Rook, and Winter Fall! Team up with other participants or select the “Private Event” option while booking to have the room to yourselves.


7. Go Shopping Along the River

Old Mill District Bend, OR

Photo Courtesy of Nate Wyeth via the Old Mill District

The vibrant and scenic Old Mill District is an ideal date night destination, whether you’re looking for excellent dining, shopping or entertainment options — or all of the above! Nestled along the sparkling Deschutes River, the Old Mill District is a mixed-use area known for its wonderful shops, galleries and restaurants. Take in the breathtaking views of the river, pop in and out of the many shops in the district, admire the beautiful work of local artists at the art galleries, grab a bite to eat at one of the fabulous restaurants, and unwind with a glass of wine (or do some tasting!) at Naked Winery or Va Piano Vineyards. The Old Mill District is the perfect one-stop-shop for all your date night needs!


8. Relax With a Couple’s Massage

Spa Brasada Bend, OR

Photo Courtesy of Spa Brasada

A relaxing couple’s massage at Spa Brasada is an excellent cozy winter date idea. This resort spa is the perfect place to indulge your senses, whether you are staying at the luxurious Brasada Ranch for a romantic getaway or you are just stopping by for the day. Rest in the relaxation room with a fireplace and enjoy access to the men’s and women’s lounges complete with lockers, steam rooms, fresh locally made snacks, and their signature Lavender Honey Shortbread Spa Cookies. Choose from the array of innovative body and beauty treatments at Spa Brasada, from their signature traditional Swedish massage to their Lemongrass Mimosa Body Scrub, and other luxe offerings. The special Winter Wonderland Spa Package is an excellent option for two guests and their High Desert Spa Package is an excellent way to warm up during the winter months.


9. Sip on Local Coffee

Coffee Shops in Bend, OR

Keep things casual with a coffee date at one of the best coffee shops and roasters in Bend! Indulge in conversation while you sip on local coffee and snack on a pastry or small sandwich. Bend has some incredible coffee shops on its roster, like the bright and modern Companion Coffeehouse and the cozy bookstore-meets-coffee-shop that is Dudley’s Bookshop Cafe! Catch up with your long-time sweetheart or get to know your new date by heading to a cozy coffee shop in town.


10. Go Wine Tasting — For FREE

The Wine Shop and Beer Tasting Bar Bend, OR

Photos Courtesy of The Wine Shop and Beer Tasting Bar

The Wine Shop and Beer Tasting Bar is not only renowned for their excellent selection of wine and beer. They are praised in the industry for allowing guests to sample 2-ounce tasters from any of the 30 wines in their wine bar without paying a dime. With over 600 labels of wines from around the globe and 16 tap handles of award-winning Belgian and craft beer, cider and mead, you are bound to discover a libation that appeals to your particular palate. Pair your drink of choice with a selection from their extensive charcuterie and artisanal cheese menu, enjoy your evening in their comfortable environment, and grab a few bottles to go to sip on another night!


11. Pick Up a New Skill (Like Cooking!)

The Kindred Creative Kitchen LLC Bend, OR

Try your hand at gourmet cooking at The Kindred Creative Kitchen LLC. Their adult workshops and classes cover a wide variety of seasonal topics changing on a weekly basis. These hands-on and technique-based classes are taught by Chef Morris, an expert chef with nearly 20 years of experience in the restaurant industry. This is an excellent opportunity to learn a new skill, meet new people, and enjoy amazing food (sometimes with a beer and wine pairing!) all the while.


Love is in the air!

What’s your favorite wintery date night idea in Bend? Let us know in the comments below!

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About the Author

Courtney Itami

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