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Romantic Road Trip in Bend, Oregon

Viewed by 82 travelers

Day 1: Romantic Getaway

Bend, Oregon

8:00AM

Breakfast at McKay Cottage Restaurant

Indulge in a cozy breakfast at McKay Cottage to start your day with delicious comfort food.
Drive or walk to Drake Park for a leisurely morning by the Deschutes River.
$$, 1 hour

10:00AM

Stroll through Old Mill District

Take a relaxing walk through the charming Old Mill District, shop at boutiques, and enjoy the scenic views along the river.
Drive to Old Mill District, park and walk around the area.
$, 2 hours

12:30PM

Lunch at Greg's Grill

Savor a delightful lunch with a view of the Deschutes River at Greg's Grill, known for its fresh seafood and American cuisine.
Drive to Greg's Grill at the Old Mill District.
$$$, 1.5 hours

2:30PM

Visit Pilot Butte

Head to Pilot Butte for a romantic hike and enjoy panoramic views of Bend and the Cascade Mountains.
Drive to Pilot Butte State Scenic Viewpoint for a romantic hike.
$, 2 hours

5:30PM

Watch the Sunset at Shevlin Park

Experience a breathtaking sunset at Shevlin Park, a perfect spot for a romantic evening stroll surrounded by nature.
Drive to Shevlin Park for a picturesque sunset view.
$, 1.5 hours

7:00PM

Dinner at Ariana Restaurant

End your day with a romantic dinner at Ariana Restaurant, a fine dining establishment known for its elegant ambiance and exquisite cuisine.
Drive to Ariana Restaurant for a memorable dining experience.
$$$, 2 hours
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More About bend oregon

Trip Packing List: Bend, Oregon — April 4–9, 2026
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Trip Packing List: Bend, Oregon — April 4–9, 2026
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