🍷 Favorite Fall Date Nights in Bend, Redmond & Sunriver

🍷 Favorite Fall Date Nights in Bend, Redmond & Sunriver

🍷 Favorite Fall Date Nights in Bend, Redmond & Sunriver

When the air turns crisp and the leaves start to glow, Central Oregon becomes the perfect backdrop for cozy, romantic date nights. Whether you’re sipping warm drinks by the fire, enjoying live music, or sharing a bottle of wine, fall evenings here feel extra special. From Bend to Redmond to Sunriver, here are some of our favorite ways to spend a date night this season.

🌙 Bend Date Nights

1. Stroll Through Downtown Bend + Drake Park
Start your evening with dinner downtown (try Zydeco for elevated comfort food or Ariana for a fine dining experience). Afterward, bundle up and take a hand-in-hand stroll along Drake Park, where the golden trees reflect in the Deschutes River.

2. Wine, Music & Theater
Bend is full of intimate wine bars, like The Wine Shop & Beer Tasting Bar or Stoller Wine Bar, where you can sip Pinot by candlelight. Check the Tower Theatre schedule for live performances to cap off your night.

3. Old Mill District – Drinks & River Walk
The Old Mill District is a perfect blend of cozy and chic for date night. Start with tropical-inspired cocktails at Rapa Nui Tiki Bar or step into the moody, romantic vibe at Lady Bird Cultural Society for craft cocktails and small bites. Afterward, wander the riverfront paths, where the fiery fall foliage glows against the Deschutes.

🌙 Redmond Date Nights

4. Beyond the Vine Wine Bar
This boutique wine lounge is perfect for unwinding with a curated glass of wine or craft cocktail. Pair it with a local charcuterie board and enjoy the cozy ambiance.

5. The Rooftop at SCP Hotel
Watch the sunset over the Cascades from The Rooftop, one of Redmond’s most romantic spots. Warm firepits, craft cocktails, and mountain views make it a fall date night favorite.

6. Grace and Hammer
Share a wood-fired pizza in this historic church-turned-restaurant. The atmosphere is unique and welcoming, with delicious food made for sharing. This is by far one of my personal favorites in Redmond, love the cozy booth or the outdoor seating.

🌙 Sunriver Date Nights

7. Dinner at Marcello’s Cucina Italiana
For a romantic, cozy dinner, head to Marcello’s Cucina Italiana in The Village at Sunriver. This longtime local favorite serves Italian classics, perfect for warming up after a crisp fall day. Share a bottle of wine, split a plate of pasta, and linger over tiramisu for two.

8. Sunriver Brewing Co. Dinner & Drinks
For a laid-back but delicious night out, head to Sunriver Brewing Co. for craft beers and hearty fall dishes. It’s the perfect place to relax after a day of outdoor adventures.

9. Stargazing at the Sunriver Observatory
End your evening by looking up at Central Oregon’s famously clear skies. The Sunriver Nature Center & Observatory offers stargazing events that make for a truly magical fall date night.

💫 Make Your Date Night a Getaway

Why stop at one evening when you can turn your date night into a romantic getaway? Our Central Oregon vacation homes feature cozy fireplaces, bubbling hot tubs, and beautiful forest views—perfect for fall escapes.

🍂 Fall Special: Stay 4 nights or more from September 1 – November 16 and save 15%.
🦃 Thanksgiving Special: Stay 5 nights or more November 21 – 30 and save 15%.
❄️ Winter Special: Stay 4 nights or more January 20 – March 20 and save 15%.

👉 Browse our homes and start planning your romantic getaway: Homes with Fireplaces