An Urban Adventure Awaits in Bend


Distance from Bend: 0
Distance Covered: 7.5 miles
Time: 4 to 6 hours
Activities: Hiking, dining, sightseeing
Difficulty: Very easy

I’ve always found one of the best ways to really learn a city is to take to the streets for an urban hike. Bend has lots of cool pocket neighborhoods, buttes, parks and green spaces, so load up your backpack for a day to explore the sidewalks and trails of Bend.

Lets start our day off right with a trip to one of my favorite breakfast places in Bend, McKay Cottage. Their bakery is one of the best in town, and if you don’t want to try one of their incredible Benedict breakfasts, I would highly recommend the Stuffed French Toast – stuffed that is with creamy Italian mascarpone cheese and topped with strawberries. YUM!

From there we’ll walk right across the street into Sawyer Park and cross the Deschutes River. Sawyer Park is a great place linger and check out the river and cool rock formations along the water. You can fish or bird watch, but we have miles so go, so we’ll head out along the Deschutes River Trail, which takes us past the greens at Rivers Edge Golf Course. 

We meet up with the river again and walk the gravel path to First Street Rapids, a popular spot for kayakers to practice their roll. A new bridge spans the water and leads us along the trail to the east side of the river. We’ll make our way through Pioneer Park, and its lush green grass, to downtown Bend. 

Deschutes River Trail near First Street Rapids

Stop in and do some shopping, or take a rest on the grass and enjoy the view of the mountains behind the iconic Mirror Pond. We’ll continue on the river trail through Drake Park. The park is a popular destination year round with music, performances, special events and usually some slack-lining and frisbee tossing going on.

Drake Park in Downtown Bend on the Twin Bridges Scenic Bikeway in Central Oregon

Now cross into the Old Mill Neighborhood; these homes were some of the first built in Bend when we really were a mill town. Riverfront is a quiet and beautiful street with a very popular stop, the Rock Art Guy. Greg Gifford’s (on the corner of Hixon Avenue and Riverfront) makes fun rock sculptures of kayakers, bikers, golfers and more. You’ll see his art all around town.

We’ll continue to the footbridge that crosses the Deschutes River and into Columbia Park. If you have any little ones with you, they will probably want to climb on the pirate ship in the playground. This neighborhood park is a great place for a pick-up soccer game or just relaxing and watching the day pass by.

Continue up Cumberland Avenue and take a right on 16th Street, and a quick left on Elgin Avenue to reach Overturf Park. This is one of the best kept secrets in town. A butte hidden in a neighborhood with an awesome view of the city…complete with a fenced dog park and trails. Make your way up, up, up to the top, and head south until you come to a large rock outcropping. It’s time to enjoy the view!

View from Overturf Park

After we are rested up, we’ll make our way back to the river the way we came, and once we hit Columbia Park, will head south on the west side of the river to the Old Mill District. We’ll walk near the Colorado Street Bridge which is the future site of a whitewater play park, a very exciting development for Bend!

Make your way past the Les Schwab Amphitheater, which also happens to be a great place to stop and fly a kite if there aren’t any events going on. The grassy slopes and consistent wind make it an ideal spot. We’ll cross the river for the fifth and final time of the day and head into the Old Mill District. Lots of shopping and dining options here, but I have our final stop on our horizon…Crux Fermentation Project lies just on the other side of the popular shopping district. 

Old Mill District near downtown Bend, Oregon

We’ll cross through to Bond Street, then take a right onto Industrial Way and head up the hill to Crux. Crux hands down has the best view in town. If you have timed it right to arrive at sunset, you will enjoy a happy hour beer with a stunning view of the Cascade Mountains. 

Time to relax, put the feet up, enjoy a craft brew and soak in your urban hike!

Renee Patrick
Renee Patrick
Renee Patrick likes to be on the move: from over 6,000 trail miles hiked (including thru-hikes on the Appalachian and Pacific Crest Trails) to her current mission of mastering the sport of packrafting, you can find her on the trails, mountains, rivers or in the coffee shop (or pub) planning her next trip. When not hiking, camping or paddling she works as a writer and graphic designer in Bend. Follow her adventures at
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