Plan a Great Date for You and Your Boo in Bend, Oregon

Aside from great company, sharing new experiences is one of the best ways to have fun together and to pull off a date to remember. Whether it’s your first date or your 50th anniversary, your new lover or a new friend, here are some great date ideas for smile-making memories in Bend.

Eight Great Dates:

Date Idea #1 – Miles of smiles then spa

Go for a day hike together, stroll through Shevlin Park, trek alongside the Deschutes River, or rent snowshoes and meander around Wanoga Sno-Park in the Cascade Mountains. Continue the mini-retreat together at Radiant Day Spa where a massage will leave you fully relaxed. After that, continue the adventure at Anthony’s at the Old Mill and try one of their Best of the Season local selections.

Date Idea #2 – Movie and a Dinner

Always a classic right? Plan ahead and get tickets to one of this season’s top blockbusters or one of the live simulcast performances from Fathom Events at Regal ScreenX & IMAX in the Old Mill District. Following the film, take yourselves over to Lady Bird Cultural Society and cozy up in the posh, Chinoiserie cocktail lounge for eclectic cocktails, shareable appetizers and wonderful conversation.

Date Idea #3 – Take each other for a spin at The Pavilion

Grab a latte or cocoa to go at Sisters Coffee Co. and lace up together for a skate date at The Pavilion. In the winter months, the ice skating arena offers Open Skate opportunities perfect for gliding together on blades, or for the less experienced, helping each other stay upright as you circle and twirl. That giddy feeling could be the effects of open air and the simple joy of play.

Date Idea #4 – Skip the tackle box and try a fly casting class

Here’s a fun way to try things out with the one you’re angling. Confluence Fly Shop hosts an array of classes from on-the-water spey casting workshops to beginner fly tying and aquatic entomology. Most classes are held on the river near the shop, which is a convenient location to learn about our local ecosystem and then mull things over while swilling a bevie from Confluence’s 8-tap bar!

Date Idea #5 – Get crafty in the kitchen

Swing by Kara’s Kitchenware and draw inspiration for you and your partner’s next great dinner party. Find the right cookware to make delicious crepes or Neapolitan pizza in a new Roccbox pizza oven, or find inspiration by participating in one of her famous cooking classes! Trust us, you’ll come home with new kitchen tools you can’t wait to use!

Date Idea #6 – Seek out adventure at REI

REI offers a series of ongoing classes covering a variety of outdoor activities, including GPS navigation, bike maintenance, winter camping and backpacking. Why not register the two of you for an evening of discovery and learning together? You can put your new skills to good use with a follow up plan to seek out one of the many geocaches nearby in the Old Mill District.

Date Idea #7 – Sip and savor wine tasting

The Old Mill District is home to two regional vineyard tasting rooms Evoke Winery and Va Piano Vineyards Wine & Champagne Bar. Evoke Winery may be the perfect place for conversation ice breakers with wines labeled Cliché Rose and Never Have I Ever Riesling. Va Piano produces elegant, balanced wines, focusing on Cabernet Sauvignon and Syrah, and they recently added champagne to their already stellar sipping menu! Both offer the perfect space to enjoy their outdoor patios and river views while you sip and savor!

Date Idea #8 – Enjoy an art filled walkabout 

Stroll through the Old Mill District and seek out the various pieces of public art that dot the landscape. You’ll find four pieces from the Old Mill District’s own Tin Pan Alley collection, Japanese artist Yuya Negishi’s dragon mural and cascading stair project, and Sisters painter/storyteller/musician Dennis McGregor’s acclaimed “You Stole My Name” collection. Be sure to pop in and meet the makers in the art studios and galleries sprinkled throughout the Old Mill District including Lubbesmeyer Art Studio & Gallery, Tumalo Art Co., The Stacks Art Studios & Gallery and Amejko Artistry in the little red shed.

A couple happily strolling into Lady Bird Cultural Society with rays of sunshine in the background.