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My itinerary for a perfect day in Bend, Oregon

old mill district

I’m visiting my parents in Kauai this week, which has me thinking a lot about vacation planning. Several times a week, I’m asked to come up with the perfect vacation itinerary for travelers visiting Bend.

My suggestions vary widely depending on whether you’re a beer geek seeking tips for navigating the Bend Ale Trail, or someone seeking family-friendly vacation ideas for summer or for chillier times of year.

But if you asked me straight up how I’d plan my very own perfect day in Bend, Oregon, here’s what I’d tell you.


6:30 a.m. Visit the dog park

I’m a morning person, and so is my dog (though she prefers to mask her person-ness beneath fur and paws). Bend was named the nation’s dog-friendliest city by Dog Fancy magazine, and the town boasts an impressive seven off-leash areas, but my personal favorite is Bob Wenger Memorial Off-Leash Area. It spans 17 fully-fenced acres filled with trees, trails, grassy areas for fetching, and even a spray park to frolic in when the weather is warm. It’s a great spot to stroll and enjoy the sunrise in the company of my favorite four-legged companion.


7:30 a.m. Breakfast at Jackson’s Corner

One of my favorite spots for a tasty, locally-sourced breakfast is Jackson’s Corner. Their original location near Downtown Bend is fabulous, but I’m especially delighted they opened a second spot in northeast Bend. That makes it a convenient post-dog park stop, and they’re open at 7 a.m. for my fellow early risers.

I’m a big fan of their biscuits and gravy made with Redmond Smokehouse gravy over housemade buttermilk biscuits, and I usually add a side of roasted seasonal veggies just to make things healthy. If I’m eating solo, I’ll probably grab a book and choose a sunny corner table or a spot next to the outdoor fire pit so my pup can join me. If I can persuade a pal to join me, I’ll talk him or her into ordering the roasted red pepper scramble (organic spinach, roasted peppers, organic eggs, and Tumalo Farms chévre) so I can sneak a bite or two.


9:30 a.m. A family hike

By this time the rest of my family should be up and around and jonesing for some outdoor fun of their own. Pilot Butte (that 500-foot dormant volcano in the center of Bend) is one of our favorite spots if we feel like sticking around town. We like to hike the paved road all the way up if we’re there during the car-free months spanning October through May, or we’ll stick with the dirt path if it’s summertime. In any case, our favorite thing to do is bring a container of bubbles and a big bubble wand with us on our hike. When we reach the top, my husband flings bubbles while the kids and dog chase them around the summit.

If we feel like venturing a bit further, we might head south toward the Newberry Volcanic National Monument for a full day of adventure, or head out to explore one of the breathtaking waterfalls in and around Bend. If it’s wintertime, a snowshoe adventure might be a fun alternative to a regular hike. In the warmer months, we love nothing more than pumping up the air mattresses so we can all float the river.


11 a.m. Shopping, sightseeing, and lunch in the Old Mill District

The Fenske-Zagurski clan enjoys a surrey ride through the Old Mill District, courtesy of Wheel Fun Rentals.

The Fenske-Zagurski clan enjoys a surrey ride through the Old Mill District, courtesy of Wheel Fun Rentals.

Now that we’ve all worked up an appetite, we’ll head to the Old Mill District for a bit of fun and sustenance. With the kids in tow, we’re likely to hit family-friendly favorites like Red Robin or Flatbread Community Oven where kids get the opportunity to make their own pizzas. During non-kid times, we’re partial to seafood hotspot Anthony’s or local favorite Greg’s Grill, where the river views are unbeatable (especially in the warm months when you can sit outside).

On a chilly day, we might spend a few hours browsing the Old Mill shops before venturing to the Regal Cinemas Theater to catch a movie. If it’s a sunny day, we might stroll along the river for a bit before renting a surrey from Wheel Fun Rentals so we can pedal around together and enjoy the scenery.


1:30 a.m. Outdoor adventures with Wanderlust Tours

I’ve been lucky enough to experience every outing offered by Wanderlust Tours, so I know an adventure with their naturalist guides is high on my list of things to enjoy on my perfect day.

A cave adventure with Wanderlust Tours makes an excellent addition to your Bend vacation any time of year.

Wanderlust recently kicked off the season for their half-day canoe trips, and since that fits nicely with today’s schedule, we’ll head out with them for the afternoon. Odds are good we’ll see otter, osprey, eagles, and more, so my wildlife quota will be met for the day. It’s also a great chance to enjoy the area’s breathtaking volcanic landscape and some of the best mountain views you’ll see anywhere.

If the day happens to be a snowy one, we could easily swap our paddles for snowshoes and head into the mountains for one of Wanderlust’s spectacular snowshoe tours. They provide all the gear, instruction, and transportation, which makes it a great way to fit in a little snow play without too much hassle.

And if the weather isn’t cooperating for an outdoorsy adventure, Wanderlust’s cave tours are another terrific option that’s available year-round.  That’s a favorite adventure for my stepson in particular, who shared his experience with the cave tour in this post.

5:30 p.m. Time to hit the Bend Ale Trail!

This might sound odd with a couple kids in tow, but there are plenty of stops along Bend’s legendary Bend Ale Trail that somehow manage to be incredibly kid-friendly without losing their edge.

My personal fave is Crux Fermentation Project, which not only boasts some of the best beer in town, but also the best grilled cheese sandwich you will ever consume in your entire life. The kids can enjoy snacking, toasting their toes at the fire pit, and chasing each other around the large grassy field while the grownups split a taster tray and enjoy a little dinner.

If we’ve got room in our bellies (and room on our Bend Ale Trail passports) for another stop, we’ll likely head for Bend Brewing Company in Downtown Bend. They’ve got a terrific kids’ menu, one of the most impressive taster trays on the trail, and a primo location right above the Deschutes River (perfect for a post-dinner moonlight stroll through Drake Park).

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