Spend The Weekend In Redmond Oregon With Us

An Itinerary For Your Weekend in Redmond, Oregon

Redmond is a hidden gem among Central Oregon destinations. Often overshadowed by towns like Bend and Sunriver. If you are looking for a Central Oregon weekend trip with under-the-radar options and access to all the best that Central Oregon has to offer, a weekend in Redmond is exactly what you need. Join us as we reveal a perfect way to spend the weekend in Redmond, Oregon.

Friday: Arrival In Redmond + Casual Local Dinner

Check In & Settle In

Arrive in Redmond, get settled into your vacation home, and take a moment to enjoy the slower pace. Summer evenings are long here, so there’s no rush.

We have several Eagle Crest vacation rentals, perfect for a weekend getaway in Redmond.

Dinner: Keep It Easy

Start your weekend in Redmond with something casual and local:

• Wild Ride Brewing – Spacious patio, laid-back vibe, and crowd-pleasing food options
• Blacksmith Public House – Elevated pub fare with a welcoming atmosphere
• Feast Food Company – Seasonal, thoughtfully prepared dishes with a local focus

After dinner, head back to your vacation home to unwind under the stars.

Saturday: Outdoor Adventure + Downtown Redmond

Morning: Coffee & Breakfast

On the first morning of your weekend in Redmond, we recommend fueling up at one of these local restaurants before a big day:

• Junction Roastery – Locally roasted coffee, breakfast bites, and a relaxed atmosphere
• One Street Down Café – Cozy sit-down breakfast favorites
• Brand 44- The perfect stop for a filling breakfast before your day at Smith Rock.

Late Morning: Smith Rock State Park

Just minutes from Redmond, Smith Rock is a must-see on any trip to Central Oregon:

• Scenic hiking trails for all levels
• River views along the Crooked River
• World-class rock climbing and iconic Central Oregon landscapes

Tip: Go early in summer to beat the heat and crowds.

Lunch: Picnic or Patio

Grab lunch in town or enjoy a picnic near Smith Rock before heading back to Redmond.

Afternoon: Explore Downtown Redmond

Spend the afternoon strolling downtown:

• Local shops and boutiques
• Art murals and small galleries
• Seasonal farmers' markets and community events

If you’re traveling with kids, nearby parks and open green spaces offer an easy break.

Dinner: Outdoor Dining

Redmond’s outdoor dining scene shines. Take advantage when the weather is nice:

• The Dry Canyon Club – A newer food truck hub with plenty of open-air seating
• Grace & Hammer – Elevated comfort food with outdoor options
• Diego’s Spirited Kitchen – Southwestern flavors and patio seating

Evening: Relax at Home

End the day back at your vacation rental:

• Board games or movie night with the kids
• A drink on the patio as the sun sets
• A soak in the hot tub once everyone winds down

Check out our Eagle Crest Resort vacation rentals for the perfect place to stay on your weekend in Redmond.

Sunday: Easy Morning + One Last Adventure

Morning: Slow Start

Ease into Sunday with:

• Coffee and breakfast at Junction Roastery
• Or a relaxed breakfast back at your vacation home

Late Morning: River or Trail Time

Choose one last outdoor outing before heading home:

• Crooked River trails for a scenic walk
• Steelhead Falls for a short but rewarding hike

Lunch & Departure

Have lunch in Redmond or grab something to-go before starting your drive home.

Why Plan A Stay in Redmond?

Redmond offers:

• Easy access to Bend, Smith Rock, and Sisters
• Less congestion and easier parking
• A growing dining scene with outdoor seating
• A relaxed, family-friendly atmosphere

Staying in a Redmond vacation home gives you space to spread out while keeping Central Oregon’s best attractions close by.

Plan Your Redmond, Oregon Getaway

Whether you’re visiting for outdoor adventure, family time, or a low-key getaway, a weekend in Redmond delivers an experience that’s equal parts fun and refreshing.

👉 Explore our Eagle Crest Resort vacation rentals in Redmond and start planning your ultimate weekend trip today.