Wine Tasting at Va Piano Vineyards

Indulge in a romantic evening of wine tasting at Va Piano Vineyards. Located in the heart of downtown Bend, this boutique winery offers a cozy and intimate setting for couples to enjoy a selection of handcrafted wines. Relax on the outdoor patio or cozy up by the fireplace as you savor the flavors of their award-winning wines. Alternative options: Maragas Winery, Faith Hope & Charity Vineyards

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Outdoor Movie Night at The Tin Pan Theater

Experience the magic of a classic movie under the stars at The Tin Pan Theater. This intimate outdoor theater hosts movie nights throughout the summer, providing the perfect setting for a cozy date night. Grab a blanket, some popcorn, and snuggle up with your loved one as you enjoy a film under the night sky. Alternative options: Regal Old Mill ScreenX & IMAX, McMenamins Old St. Francis Theater

Sunset Picnic at Pilot Butte State Park

Pack a picnic basket and head to Pilot Butte State Park for a romantic sunset picnic with sweeping views of the city. Enjoy a leisurely dinner as the sun sets behind the Cascades, casting a warm glow over the landscape. This serene and picturesque setting is the perfect backdrop for a memorable date night. Alternative options: Shevlin Park, Drake Park

Couples Massage at Anjou Spa

Treat yourself and your partner to a relaxing couples massage at Anjou Spa. Unwind and de-stress together with a customized massage experience designed to soothe your mind, body, and soul. Enhance your date night with a luxurious spa treatment that will leave you both feeling rejuvenated and connected. Alternative options: Jinsei Spa, Spa W

Brewery Tour at Deschutes Brewery

Embark on a brewery tour at Deschutes Brewery, one of Bend’s most iconic craft breweries. Learn about the brewing process, sample a variety of beers, and enjoy a behind-the-scenes look at this local favorite. After the tour, relax in the taproom and savor a delicious meal paired with your favorite brew. Alternative options: 10 Barrel Brewing Co., Boneyard Beer

Cooking Class at The Well Traveled Fork

Get hands-on in the kitchen with a cooking class at The Well Traveled Fork. Learn new culinary skills, experiment with fresh ingredients, and create a delicious meal together under the guidance of experienced chefs. This interactive and fun date night activity is perfect for food-loving couples looking to spice things up in the kitchen. Alternative options: Naked Winery, Immersion Brewing

Live Music at The Capitol, Bend

Immerse yourself in the vibrant local music scene with a live performance at The Capitol in Bend. This historic theater hosts a variety of musical acts, from local bands to touring artists, providing a lively and entertaining date night experience. Grab a drink at the bar and enjoy a night of dancing, singing, and unforgettable memories. Alternative options: Volcanic Theatre Pub, M&J Tavern

Stargazing at Pine Mountain Observatory

Escape the city lights and journey to Pine Mountain Observatory for a magical evening of stargazing with your partner. Located just outside of Bend, this observatory offers breathtaking views of the night sky, perfect for romantic moments under the stars. Pack a telescope, blankets, and hot cocoa for a cozy and unforgettable date night. Alternative options: Sunriver Observatory, Oregon Observatory at Sunriver

Art Night at DIY Cave

Unleash your creativity with an art night at DIY Cave, where you can explore various art mediums and create your own masterpiece together. This hands-on date night activity allows you to express your artistic side while bonding with your partner in a unique and inspiring environment. Get ready to get messy and make memories that will last a lifetime. Alternative options: Cheers Pablo, Tumalo Art Co.

Hot Air Balloon Ride with Big Sky Balloon Co.

Soar to new heights with a romantic hot air balloon ride over the stunning landscapes of Bend with Big Sky Balloon Co. Experience breathtaking views of the Cascade Mountains, Deschutes River, and lush forests as you drift peacefully through the sky with your loved one. This unforgettable adventure is sure to create memories that will stay with you forever. Alternative options: Big Sky Balloon Co., Sunriver Balloon Adventures