Several murals in downtown The Dalles depict the area’s rich history.(Photos by J. Maus/BikePortland)

While most of the attention for cycling in The Dalles is focused on the stellar roads outside the city, you’ll be missing a lot if you don’t explore the town itself. Put another way; you don’t have to wear spandex or be ultra-fit to explore the cool things this town has to offer. From history, to local watering holes, to big views of the Gorge, a bike is all you need to take it all in.

After being here a few days, I heard about several “must-see” destinations over and over again. So today, I headed out and connected a bunch of them up into a tour. I had a great time doing it myself, so I figured it’d be worth sharing.
If you’re here on a weekday (they’re closed on weekends), I recommend starting from The Dalles Chamber of Commerce and Visitor Center. You’ll meet nice folks there who will answer your questions, and they also have all the good brochures and info you’ll need to learn about the area. I started my tour from Cousin’s Country Inn, a very nice place to stay (and eat!) if you plan to be here overnight.

Ready? Let’s go…

From the Chamber (or anywhere downtown for that matter), head up W 3rd Place to Trevitt Street. At Trevitt and 6th, you’ll see the historic Bennett House (a Queen Anne Victorian built in 1899) and you’ll hear the rustling of Mill Creek just to the west.

This house was built in 1899 for Alfred Bennett, an Oregon Supreme Court Justice and congressional candidate.

Shift to your easy gear and head straight up the hill on Trevitt Street. If the climb takes your breath away, stop and turn around to take in the view of the Columbia River. Or, stop and check out the old houses in this historic residential district. If the season is right, you’ll see cherry trees in bloom.

Hang a left on W 15th Street and go one block to Garrison Street where you’ll see the Fort Dalles Museum on your right. This is the oldest history museum in the state of Oregon. The building on the site is the Surgeon’s Quarters that was part of a full-fledged U.S. Army fort built in 1850. It was active until 1867 and turned into a museum in 1901. I pulled my bike right up onto the porch; but the volunteers inside assured me they would apply for a Bike Friendly Business certification and that bike racks are on the way. It’s worth parking and paying the $5 admission fee to see the wonderful collection of artifacts, photographs, and maps inside. Make sure to venture upstairs to peer out of the Gothic revival windows and see several rooms full of historical objects. The expansive, grassy grounds of the museum would be a perfect place for a picnic or a brief respite to ponder Oregon’s rich history.

The Surgeon’s Quarters is the only building that remains from Fort Dalles.

From the museum, head downhill on Garrison Street and then make a right at 14th. Then take a left on Union Street and head downhill. Before you get downtown, stop at Union Park (on your left) just after 7th Street. There’s a rock at the entrance of the park that marks the “End of Oregon Trail.” It turns out this proclamation is a sore spot for The Dalles civic boosters and history buffs. Oregon City also claims to be the end of the Oregon Trail, but The Dalles holds this distinction from a technical standpoint. When I brought this up to the museum volunteers, I clearly struck a nerve. “They’re [Oregon City] at the end of Barlow Road, not the Oregon Trail!” one of them vehemently stated.

Continuing down Union Street, make a right on E 4th. When riding in downtown The Dalles, you’ll want to avoid E 2nd and 3rd whenever possible. Those streets make up a couplet that is very auto-centric and not very good for cycling. On 4th, you’ll notice the historic facade of the Civic Auditorium, built in 1921. Also, keep an eye out for a few amazing old Victorian houses (complete with picket fences) before making a left on Jefferson Street.

I love these old signs on Union Street.

Victorians on 4th.

From Jefferson you’ll go right on E 3rd and head east. The road is a bit stressful here, and you’ll be in close quarters with people driving cars, so stay alert. When you come to the roundabout, remember to take the full lane. People slow way down going through it and I never had any problems sharing the road.

Entering the roundabout on the east side of town near Sunshine Mill winery. The bike lane ends, so you’ll want to take the lane.

At this point in the tour, you can choose one of two options: Big Jim’s Drive-In for burgers and ice cream, or the Sunshine Mill/Quenett Winery Tasting room (or I guess you could do both if you’d like!). Big Jim’s is a local institution that serves up robust and tasty hamburgers and homemade ice cream in classic American style. The only catch is that it’s 1 1/2 miles east of downtown and there’s also a railroad supply factory nearby that emits a creosote odor that can be nasty depending on wind direction. Personally, I think it’s worth it to head to Jim’s, because you get great food and a nice view of the river on the way out and back.

Worth an extra three miles? You decide.

The Sunshine Mill tasting room is another awesome spot that I highly recommend. The owners converted a working mill (formerly owned by Nabisco) into a very cool hang-out. They incorporated much of the old factory equipment into the tasting room decor and there’s even an old engine built by some guy named Thomas Edison. Quenett is known for their Copa Di Vino, which are single-serving wines in plastic cups. They’re perfect for cycling because they’re light, unbreakable, and you can fit several of them in your jersey pocket, pannier or backpack.

Interior of the Sunshine Mill tasting room.

Copa di Vino: Perfect for cycling.

Sunshine Mill Winery employee Vicki Byrd.

After you’ve had a taste of wine, it’s time to head west on East 2nd Street, the other half of the downtown couplet. As you roll by, take a look at some of the many historical murals and check out the local businesses on The Dalles’ main street which include: The Dalles Iron Works, a modern-day blacksmith shop; Clock Tower Ales, a pub with tons of craft beer housed in a historic court house; Baldwin Saloon, which first opened in 1876 and still retains much of its original charm (and artwork!); and Petite Provence, an authentic french bakery that also has a location on Alberta Street in northeast Portland.

Clock Tower Ales is a popular spot. And they even have a bike rack out front (albeit not a very good one).

Entrance to Baldwin Saloon.

Inside Baldwin Saloon.

From 2nd, you’ll hang a right on Union Street which will take you under I-84 and onto the Riverfront Trail. In my opinion, this path is the marquee attraction for cycling in The Dalles. The total length is 10 miles, of which about 8-9 miles is complete (there’s just one small gap remaining). On this tour, you’ll head west from the cruise ship dock at Union Street and enjoy six miles of uninterrupted biking/walking path that winds through a variety of landscapes and potential adventures.

The new I-84 underpass, which connects you right to the Riverfront Trail.

Hard to believe that just a few days ago I had no idea this stellar Riverfront Trail existed.

Your first must-stop location along this path is Lewis & Clark’s Rock Fort Campsite. The adventurous duo camped in this rocky fortification in 1805 and it’s a great place to read about the history (thanks to the excellent signage) or have a picnic among the grass and rocks along the riverbank.

After Rock Fort, the Trail weaves through industrial areas for a mile or two before getting back to the riverfront. This section is forgettable except for passing by the Oregon Cherry Growers factory. It would be fantastic if they offered tours, but even without them, you can still imagine all the local cherries processed here and enjoy a few deep breaths of the sweet cherry aroma as you pass by.

This is the only bad part of the path; but it doesn’t last too long.

Overall, I was extremely impressed with the Riverfront Trail. The views along the Columbia are world-class and the path itself is consistent and smooth all the way to the Gorge Discovery Center (its western terminus). Along the way, you can stop and scramble among the rocky cliffs, trails, and even sandy beaches. I also recommend taking time to stop at the Imagination Garden (mile 2.8, you’ll notice the mosaics) and Taylor Lake (mile 1.1.). Other highlights include tribal fishing platforms, educational signage, the wetlands near Chenowith Creek, and simply breathtaking views of the Gorge right beyond your handlebars.

Chenowith Creek.

The Trail is popular with the locals.

The western end of the Riverfront Trail is really incredible. There are even nice benches to soak up the view.

Take the path over to Taylor Lake, where there’s a bridge and some rocks to play on.

The Columbia River on one side, Taylor Lake on the other, and dirt trails to explore. Awesome!

At the Discovery Center there are few old pioneer artifacts along the trail.

After looping around the Discovery Center, you’ll connect onto the Historic Columbia River Highway to return to town. This loop is just under 17 miles, and I’ve mapped it out at RideWithGPS.com.

If you’re able to try this out, I think you’ll agree with me that The Dalles has a lot to offer when it comes to cycling. Most of this loop (and certainly the entire Riverfront Trail) is perfect for families. Head out here and try it out!

— This story is part of our special reporting trip to The Dalles. See more coverage here.

Again, looks great.
I was wondering if you have heard any talk in The Dalles of people supporting the return of the Pioneer rail line?
As Amtrak is seemingly getting more bike friendly, a route like that to the Dalles and further east seems like it would help bike tourism as well.
It would be great to be able to get on the train for an hour/hour and a half with the bike and then get off and stay in these towns for a few days.
The whole route is outlined here:

Given that I-84 has capacity, have the cities east of Portland in the Gorge considered a shuttle similar to Mountain Express out of Sandy, or the Breeze shuttle to Bend? They could have a few morning departures from Downtown and Gateway in Portland, stopping in Cascade Locks, Hood River, and the Dalles. There would be an afternoon and evening return option. Once ridership is built up, it would be easier to justify a train from Portland.

Since I live in The Dalles I would like to point out two omissions to your delightful article: On Second Street, heading west, is Oregon’s oldest book store, Klindts’ Booksellers, complete with original wooden floors and BOOKS!
The other is an eatery on the Waterfront Trail just a little west of the Industrial area. It has outdoor seating right on the River, but the best part is the “back yard”, a fenced-in picnic table area where you can get the biggest, best burgers in town and tap beer. I don’t know whether they have a bike rack yet, but you can probably wheel your bikes in past the pool tables and keep them safe in the beer garden.

The grade school across Trevitt from the Fort Dalles Museum was name after Col Wright (fort commander in 1849), and is located on the old parade grounds. There used to be an old oak tree in front of the school, and Colonel Wright would bound the drunk soldiers to that oak as punishment (my Col Wright playground teacher would suggest the same punishment at times in the 60’s ;-) ) .
If you climb Trevitt and Scenic Drive you’ll end up at Sorosis Park. The 45 acre park is a natural ponderosa pine forest with great views of the gorge. There’s an memorial rose garden, and 30 foot tall marble fountain that was used as horse/dog/people drinking fountain in town, and then re-assembled at Sorosis Park.

“Hard to believe that just a few days ago I had no idea this stellar Riverfront Trail existed”

cut yourself some slack! There are miles of beautiful roads we will ride on who’s name we will never know. There are miles of beautiful roads within cycling distance of Portland (as is The Dalles at 87 miles) that we will never ever see. You have been spending more time on that white bicycle lately and that’s what counts. I see this bicycle every time I log into ridewithgps.com, so maybe you have been using maps as well as chain lube?

Dixie Mountain, Pittsburg Rd., Marmot/Lolo…
Year by year, It is really fun watching you discover and publicize the regions bicycling facilities and roads. You discovered The Dalles!

Yes, bring back The Pioneer! It left Portland in the AM with PM train returning west; just the reverse of The Empire Builder across the River.
15 years ago we found a great rental up Mill Creek Valley and really enjoyed The Dalles, with side trips to Dufur (“Ask not what Dufur can do for you, ask what you can do for Dufur!”), Friend and the White River Falls, Columbia Hills State Park, Maryhill Museum and Curves, and Wishram on the WA side (the bridge is free), and on and on.
Be ready for some wind…and farther east, LOTS of wind turbines.