Valentine’s Day is just a couple weeks away, though you don’t need a cheesy holiday to plan a special date in Bend. In case you haven’t heard, Bend was just named one of the nation’s ten most romantic cities by Livability.com!

There are oodles of unique ways to enjoy a romantic outing with your sweetie in this Central Oregon paradise, and my gentleman friend (more commonly known as copywriter/photographer Craig Zagurski) set out with me to try a few. Here are our top three ways to canoodle with your honey in Bend!

Get SWANKY with dinner & jazz night

Dressed up for Jazz Night at the Oxford!

I adore live music, though jazz isn’t usually my favorite. But after three years of hearing everyone gush about the fabulousness of Jazz at the Oxford, I caved.

It was hardly a sacrifice.

I’ve spent a lot of time in the upscale Oxford Hotel, and enjoyed plentiful drinks in their restaurant 10Below, but Jazz at the Oxford is an entirely different scene. We had the pleasure of catching multi-Grammy nominee Karrin Allyson in mid-January, and the place was packed.

We seized the opportunity to get dressy in cocktail attire, and many members of the audience had the same idea. If you want to break out the suit or the little black dress, this is a great excuse.

I’m not sure how the Oxford manages to pack so many people into one room and achieve an intimate, romantic vibe, but they pull it off brilliantly. The dim lighting lends a dreamy feel to the space, making it easy to grope your date’s knee under the table.

So I’ve heard.

Karrin Allyson and her amazing band.

During the show, you can order from an impressive menu of cocktails, wine, beer, and food. We opted for a couple glasses of wine and a simple charcuterie tray, while the couple beside us went for a full-on dinner including buttery clams and a thick steak.

For a truly special evening on the town, you’d be smart to book dinner reservations at 10Below either before the event (if you’re catching the 8 p.m. show) or afterward for those with 5 p.m. tickets. That way you can fully enjoy your meal without worrying you’ll plop a scallop on your lap or stab a fellow concertgoer with your steak knife. You can even book an overnight stay at The Oxford or one of countless other Bend hotels, motels and resorts listed on our Bend lodging page.

There are a couple more jazz nights in the lineup before the season ends, including shows by Mel Brown Septet (Feb. 22-23) and Tom Scott & California Express (March 15-16). Tickets range from $35-$49, and you should buy now since shows almost always sell out.

Grab a pair today, and get ready for the ultimate romantic evening!

GET ACTIVE with a romantic winter picnic

Heading out on skis for our romantic winter picnic.

Many Bend visitors come here seeking recreation, so my gentleman friend and I planned one date with this in mind.

After packing a simple lunch of apples, cheese, peanuts, and cold chicken, we headed to Pine Mountain Sports to rent cross country ski gear. Though I grew up nordic skiing, I hadn’t been out on the trail for nearly ten years. My gentleman friend, on the other hand, had never set foot on skis of any kind.

I’ll admit I worried one of us might pull a groin (thereby putting a crimp on any future romantic plans), but I needn’t have worried. The trails at Virginia Meissner were perfectly groomed and easy to follow, making our trek a snap on the Tangent Loop Trail.

The cozy warming hut with its toasty wood stove.

Even with our minimal skills and occasional spills, we made the 1.5 mile trip to our chosen warming hut in about 45 minutes. Though we’d planned to enjoy our picnic snuggled beside the hut’s wood stove, the weather was too nice to resist. We dragged a couple logs out of the woodshed and parked our butts out in the snow to enjoy breathtaking mountain views while sharing our meal.

If cross country skiing isn’t your thing, try the snowshoe trails instead. The Meissner Nordic folks do a superb job marking trails to make it clear which ones are for which use, and you end up in the same place either way.

Sitting in the snow, enjoying my picnic!

Can’t resist the urge to bring Fido on your romantic outing? There’s a warming hut at Wanoga SnoPark, too, and as long as you pick up after your pooch, he’s welcome to join you as you ski, snowshoe, or even walk off that hearty picnic.

One word of caution: though it might be tempting to pack cocoa & schnapps or even a bottle of wine, don’t forget to toss in some water, too. It’s important to rehydrate anytime you work up a sweat with your sweetie.

GET CLOSER with a cooking class for two!

Craig grates chocolate over the tiramisu as Chef Bette offers tips.

Countless studies and women’s magazines tout the romantic benefits of couples learning new skills together.

That – combined with the fact that my gentleman friend and I truly love food – is what landed us in a Well Traveled Fork cooking class with Chef Bette Fraser.

I stir the pot as Chef Bette intructs another member of the class with cutting techniques.

We joined several other couples at Chef Bette’s magnificent Bend home for an intimate evening of slicing, sautéing, and learning to prepare the perfect Valentine’s dinner. Our classmates ranged from competent cooks to those who seemed uncertain which end of the knife to hold, which is part of what made the experience so enchanting.

My gentleman friend learned to grate gourmet chocolate over a delectable tiramisu, while I worked on my technique for frying homemade corn chips to accompany our fresh fruit salsa. Looking around the cozy kitchen, I saw couples young and old sharing fond smiles as they refilled each other’s wine glasses or worked together to cut the perfect parchment heart for our fish en papilote.

Once we finished assembling the meal, we all went home hungry.

I’m kidding, of course. We all sat down and enjoyed a wonderfully romantic dinner made even more scrumptious by the fact that we helped prepare it. And we got to take home our new knowledge – not to mention easy-to-follow recipes – so we can make the same tasty meal at home where we’re less likely to offend anyone by wearing nothing but aprons and smiles.

Sorry about that, Chef Bette.

The Well Traveled Fork has tons of other great classes on the schedule that are perfect for couples looking to learn some new culinary skills together.

Fish en papilote, prepared in the perfect parchment heart!

If cooking doesn’t roll your socks, up, check out the schedule of continuing ed classes offered by Central Oregon Community College. There’s a Thai for Two massage workshop slated for Feb. 10 with a few slots left, and oodles of other offerings to suit all kinds of interests.

So what’s your favorite way to spend a romantic date in Bend? Please share!

And please have a very happy Valentine’s Day no matter how you choose to spend it!