Historical Tours

Explore The Dalles

Where Will You Explore?

Step into the stories of the past and discover the charm of The Dalles—where Oregon Trail pioneers once passed through, and history lives around every corner. Whether you’re here for a weekend or just a day, this itinerary will guide you through some of the most memorable experiences in The Dalles.

Friday: Arrival & Local Flavor

6:00 PM – Check into the beautiful R & R Guest House, a historic bed and breakfast that blends comfort with classic charm.

7:00 PM – Head to Zim’s Brau Haus, a local favorite offering hearty comfort food, craft beers, and a warm, welcoming vibe in the heart of downtown. It’s the perfect place to settle in, enjoy a great meal, and toast to the start of your weekend in The Dalles.

Saturday: A walk through history

8:00 AM – Fuel up with breakfast at Petite Provence on 2nd Street, set in a gorgeous historic building.

9:00 AM – Walk off breakfast with a downtown history tour! Highlights include:

  • Lewis & Clark’s Rock Fort
  • 15 Historic Murals throughout downtown
  • The Dalles Fire Museum at 3rd & Court
  • The Carnegie Library (now The Dalles Art Center) on 4th
  • Klindt’s Booksellers – Oregon’s oldest bookstore
  • Breezeway Boutique Antiques (west of Klindt’s)
  • Route 30 Bottles & Brews (east of Klindt’s) for a mid-morning pick-me-up

12:00 PM – Grab lunch and a craft brew at Freebridge Brewing, located in the historic Mint Building at 710 E. 2nd St.

1:00 PM – Spend the afternoon exploring iconic local landmarks:

  • Original Wasco County Courthouse
  • Pulpit Rock (E. 12th & Court)
  • Pioneer Cemetery
  • Sorosis Park – sweeping views of the Gorge
  • Fort Dalles Museum
  • Rorick House – home of poet and politician William O. Rorick

5:00 PM – Sip and relax at Sunshine Mill Winery, set in the first building in The Dalles to have electricity. (901 E. 2nd St.)

6:00 PM – Enjoy dinner and dessert at the Baldwin Saloon—a beautifully restored 19th-century saloon serving up delicious fare and old-world charm. (205 Court St.)

Sunday: Scenic Sites & Gorge Gems

8:00 AM – Start your day at Riverenza Café, a cozy café once home to the Church of Christ.

9:30 AM – Dive deeper into the region’s story at the Columbia Gorge Discovery Center (5000 Discovery Dr.), where interactive exhibits bring local history and nature to life.

12:00 PM – Cross The Dalles Bridge and head into Washington for lunch at Maryhill Winery, known for its breathtaking views and award-winning wines.

1:00 PM – Discover the nearby historical and cultural treasures:

  • Stonehenge World War I Memorial – a striking replica with a powerful story
  • Maryhill Museum of Art – world-class art in a cliffside mansion

4:00 PM – Head home with your heart (and camera) full from a weekend immersed in sunshine, stories, and the scenic beauty of Oregon’s first National Scenic Area.