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How to Plan the Perfect Weekend in Bend

Oasis Property Rentals5 min read
Sunset view of Central Oregon's Cascade range

From morning coffee at Sparrow Bakery to sunset at Drake Park, here's how our team would map out 48 hours in Bend if it was their first time visiting.

Two days isn't long. But Bend is compact enough that you can pack a lot in — if you know where to go.

Friday evening

Land, drop your bags at the rental, walk to dinner. The walkable Old Mill District works for a first night because it's hard to mess up. Spork for fusion, The Drake for upscale Northwest, Boss Rambler for craft beer and wood-fired pizza.

After dinner, grab a beer and walk the river path. The Deschutes runs right through downtown.

Saturday morning

Coffee and pastries at Sparrow Bakery. Get the ocean roll. It's their thing.

If you're an outdoors person, you have two excellent options for a half-day:

  1. Tumalo Falls — short drive, easy 1-mile loop, dramatic waterfall
  2. Smith Rock State Park — 30-minute drive, world-class climbing, plenty of moderate hikes

Saturday afternoon

Lunch at The Lemon Tree or 10 Below. Then either:

  • The Bend Ale Trail (10+ breweries, you don't need to do them all — pick 3)
  • The High Desert Museum if it's hot, or you have kids

Saturday evening

Dinner at Ariana for tasting menu, or Trattoria Sbandati for handmade pasta. Walk Drake Park before sunset for the postcard view.

Sunday

Brunch at Jackson's Corner. Then before you fly out, drive a stretch of the Cascade Lakes Highway — it's one of the most beautiful drives in the country and you'll regret skipping it.