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  • Flower Bar

    River's Place 787 NE Purcell Blvd, Bend, OR, United States

    Craft a custom bouquet with your sweetie or select a beautiful pre-made arrangement. Featuring classic roses and an array of beautiful blooms. Prices vary. No reservation required.

  • Hoodoo’s Enchanted Nordic Trek

    Hoodoo Ski Area

    Enchanted Nordic Trek Presented By FivePine Cabins & Explore Sisters Explore Sisters & Five Pine Cabins is proud to invite you and a partner to a magical evening trek at Hoodoo's Nordic Trail System! The first 50 romantic trekkers will receive complimentary goodies. Enjoy a rose, chocolate covered strawberries, and a deluxe hot chocolate station!...

  • Bistro Colette Pop-up

    Bistro Colette Pop-up
    Flights Wine Bar 1444 NW College Way Suite 1, Bend, OR, United States

    Executive Chef Jeremy Buck from Salute Restaurant & Bar joins Flights Wine Bar, creating a French themed pop-up bistro. Reservations recommended. Make reservations at flightswinebend.com/reservations

  • Valentine’s Chef Pairing Experience

    Valentine’s Chef Pairing Experience
    Willamette Valley Vineryards - Bend 916 NW Wall St, Bend, OR, United States

    Join us at the Bend Tasting Room & Restaurant for a Valentine's Day Chef's Pairings Experience, hosted by our Winery Ambassador Ashley and Chef Cuin. Bring your friends along for this exclusive wine and culinary journey, where you’ll indulge in a curated five-wine flight paired with 3 exquisite chef-created dishes as well as a delightful...

    $95

  • Ballers & Brews Sweethearts Valentine’s Play

    Ballers & Brews 20869 Redside Court, Bend, United States

    Whether you’re already a dynamic duo or just testing your doubles chemistry, this Valentine’s event is for lovers, friends, and hopefuls. Includes: 🏓 1 hour of pickleball play 🎾 All paddles & balls 🧀 A swoon-worthy charcuterie board from Bread & Bunny (per couple) 🥂 A glass of Do Epic Sh*t bubbles for each player...

  • Valentine’s Day Prix-Fixe Dinner

    Currents at The Riverhouse 3075 Business 97, Bend, OR, United States

    This Valentine’s Day, settle in for an elegant evening of seasonal flavors, candlelit ambiance, and thoughtfully crafted dishes at Currents Restaurant & Lounge. Our culinary team has curated a four-course prix fixe menu designed to be savored slowly—perfect for celebrating love, connection, and great food. Enjoy a refined, relaxed dining experience for $80 per person...

    $90

  • Austin Mercantile Sip & Serenade

    Austin Mercantile 19570 Amber Meadow Dr #190, Bend, United States

    This Valentine’s Day, fall in love over bites, bubbles, and beautiful music at Austin Mercantile. Candlelight + Live Music by Jason Burky ✨ Valentine’s Special Menu ✨ • Valentine’s Charcuterie • Beet Napoleon with Prosciutto • Meatball Skewers • Strawberry & Ricotta Bruschetta • Desserts by Messy Marvin’s Bakery: Chocolate Cheesecake with Raspberry Chocolate-Covered Strawberries...

  • Valentine’s Day Dinner & Dance Concert

    Great Hall at Sunriver Resort 57081 Great Hall Loop, Sunriver, OR, United States

    2026 continues the tradition of Sunriver Music Festival's Valentine's Day Dinner & Dance Concert. Sponsored by Sunriver Resort and Sunriver Markets and featuring the 17-piece Notables Swing Band, here’s your opportunity for a fun night out in the iconic Great Hall. All seats are reserved and tickets include a glass of wine, multi-course dinner and...

    $140

  • Valentine’s Day Dinner at Juniper Preserve

    Juniper Preserve 65600 Pronghorn Club Dr, Bend

    Celebrate your love with a curated and intimate Prix Fixe dining experience this Valentine's at Juniper Preserve.❤️ The menu is designed to be enjoyed as a journey—unhurried, intimate, and perfectly suited for the occasion. Reservations are available here.

  • Valentine’s Dinner and a Movie

    Riverhouse Lodge 3075 N Highway 97, Bend, OR, United States

    This Valentine’s Day, trade candlelit clichés for a heart-pounding, laugh-out-loud adventure at Riverhouse Lodge’s Dinner & a Movie—where romance isn’t just in the air, it’s chasing buried treasure. Arrive at 6:00 PM and settle in for an evening designed to sweep you off your feet. At 6:30 PM, dinner and the movie begin, pairing a...

    $82

  • Valentine’s Chef Pairing Experience

    Valentine’s Chef Pairing Experience
    Willamette Valley Vineryards - Bend 916 NW Wall St, Bend, OR, United States

    Join us at the Bend Tasting Room & Restaurant for a Valentine's Day Chef's Pairings Experience, hosted by our Winery Ambassador Ashley and Chef Cuin. Bring your friends along for this exclusive wine and culinary journey, where you’ll indulge in a curated five-wine flight paired with 3 exquisite chef-created dishes as well as a delightful...

    $95