I love the New York Times’ 36 Hours in [insert city name] articles, so here’s a NY Times inspired list in my neck of the woods — Bend, Oregon. Although I spent longer than 36 hours in Bend (I used to live there after all). This list is an example of some of my favorite things in Bend. (The NYT did a 36 Hours in Bend article in 2004, but a lot has changed since then. Bend is a little different these days!
Central Oregon has always been a popular place for Portlanders to escape the drizzles of the Willamette Valley. Bend boasts 300 days of sunshine per year and while Californians have been flocking to Bend for several decades, the last ten years has seen explosive growth. The upside was much needed retail development (Trader Joes, Old Mill district shopping, REI etc). And a population increase to support fantastic eateries to compliment Central Oregon’s already amazing outdoor pursuits. However, the downside was unfinished, vacant vacation home subdivisions, and nation-leading unemployment rates at the start of the 2010s. Now Bend is back on the up-and-up and seeing a new surge in younger transplants and families looking for more work-life balance. Here’s what to do with 36 hours in Bend. With a choose your own adventure style update! Summer and winter ideas!
36 Hours in Bend Itinerary
1) Old Mill District – On Foot or Bike
Start your weekend off by checking out the [relatively] new Old Mill District of Bend, on foot or bike. This area was literally the old “mill district” for timber mills in the early 1900s. It’s now an outdoor retail and restaurant space on the river, with Les Schwab Ampitheater just across the footbridge.
Unofficially, the Old Mill District is also thought of as the Deschutes River Trail – a 4 mile loop around the river of [almost] connected parks and green space. Starting at the Old Mill District, head south to Farewell Bend Park, and over the footbridge to Riverbend Park (or do longer loop over Reed Market Bridge). Then, you can continue the loop north through the ampitheater, a bit of neighborhood to Columbia Park, down the one story slide to the river trail and across the footbridge to Gilchrest Ave and south to Miller’s Landing Park. Then, past the White Water park and back to the start of your walk. Depending on the season, BYO beverage of choice and enjoy your time exploring. If you have kids en-tow the ship playground at Columbia Park or Farewell Bend are our favorites.
2) Brewery or Food Cart Happy Hour
If you didn’t already give into your hunger cravings somewhere along your riverwalk, head to 10 Barrel Brewing. If there’s a wait or you have an indecisive bunch then head across the street to The Lot. A food cart pod near Galvaston, The Lot has a selection of carts, drinks, and live music. Great for groups, as you can split up and order what you really want. This place gets busy on the weekends, so have a backup plan for taking your food to go. If you’re not walked-out, Drake park is a few blocks across the river.
3) Breweries ’til 9pm or Not Your Typical Dinner & A Movie
Depending on how much beer you’ve already had, check out one of Bend’s best – Crux Fermentation. Most tap rooms are open until 9pm. Otherwise, head downtown. One of McMenamins’ renovations, Old St. Francis School, is a one-stop shop for catching a $5 movie, pizza and McMenamins handcrafted ales. In true McMenamin’s fashion, you will find not one, but five bars around the premises. Right in downtown Bend, it’s also a convenient and kitschy place to stay. Even if you’re not spending the night (from $114), check out the Turkish style soaking pool before you leave. It’s open to non-hotel guests as well (until 8pm).
4) Downtown bars or get some sleep for an active day tomorrow
Your late-night options in Bend are still fairly limited. So either stay put at a downtown bar, or grab some drinks for your Airbnb.
In paradise, the weekends aren’t for wasting, but you’ll need to fuel up for your action-packed day. Head to Jackson’s Corner (two locations) for a casual deli/bakery option. Order the avocado toast or breakfast burrito and coffee. There’s also Mother’s Juice Cafe for a quicker and yummy order of banana bread and smoothies. Or Backporch Coffee Roasters for an early coffee and pastry before heading out on an adventure.
6) Hiking, Kayaking, Rafting, or Skiiing/Snowboarding
Summer: You really can’t go wrong in choosing an outdoor activity in Central Oregon. An easy hike from Bend is Tumalo Falls. The waterfall view is just a few minutes hike. Or you can continue the 6.5 mile hike. For a longer hike, try the Deschutes River Trail, that connects downtown to Benham Falls & Dillon Falls. Or head north to the climbing and hiking wonderland of Smith Rocks State Park. For the more adventurous, go white water rafting on the Deschutes. The Inn of the Seventh Mountain operates 2-hour trips that leave five times a day ($50). They also offer SUP & kayak tours and rentals. Or rent a tube and “lazy” float the river through town. You can also check out Mt Bachelor in summer to ride the lift up to the Pine Martin lodge. And mountain bikers can ride back down the mountain (yes, you need a pass to do it).
Winter: Head up to Mt Bachelor for a day (or half day) on the slopes. Central Oregon has much dryer snow than some other Pacific Northwest mountains. A bit more reminiscent of Colorado powder. Mt Bachelor is one of Oregon’s best ski destinations. And a day on the mountain is not cheap here. A pass will cost you upwards of $85, add on more if you’re renting skis or snowboard, taking lessons or using childcare. Not up for skiing? You can also check out the tubing snow park (tubes included).
7) Back to Bend Brewery Hopping
If you’ve had too action-packed of a day, head to the soaking pool at McMenamin’s to soak your aches away. Then, it’s brewery hopping time.
Start out with a free brewery tour at Bend’s first brewery, Deschutes Brewery, across from the Old Mill District. Tours start on the hour and 4pm is the last tour of the day. Take your time sampling, and then head north to Bend’s second brewery Bend Brewing Company, near Drake Park or to another newer brewery like Worthy, Goodlife, Boneyard, or 10 Barrel or Crux if you didn’t make it yesterday. Every year more and more breweries open in Bend, so check out Visit Bend’s Ale Trail for the latest list. If you have more than 36 hours in Bend, you can hit quite a few!
8) Dinner Downtown
Overlooking Mirror Pond, Bend Brewing has great burgers and beer (obviously). Otherwise, check out one of Bend’s longest-standing fine dining options The Pine Tavern. I remember coming here as a kid and loving the honey butter (oh the things you remember!). Spork is another great option – with Asian fusion or hit up a casual spot from yesterday.
9) Stargazing, Music, and Brews
Depending on how much fun you had brewery hopping, and if you’re not “outdoorsy-ed out”, go for an evening wander around the Old Mill District – along the Deschutes River, Les Schwab Ampitheater, and Riverbend Park. If it’s concert season, you can hear the music from around, but you have to keep walking (people used to set up lawn chairs on the east side of the river for a free concert!). If you’re less-inclined to be checking out real nightlife outdoors, stay downtown and check out a few wine bars or Bend Distillery.
10) Brunch Time!
After yesterday’s quick breakfast, try out a Bend brunch spot. Check out Chow on the west side. Another mainstay on the Bend breakfast scene, it’s a little spendier, but mighty good. Or grab a bite at one of the two locations of The Sparrow Bakery (order the Ocean Roll!). There are so many new places popping up in Bend, that your best bet for the latest and greatest is to check out Yelp or Google.
11) Downtown stroll or biking
If you still haven’t done some downtown strolling, head there. Visit Bend, has a list of historic walking tour highlights (including the Reid School – the first modern schoolhouse in Bend, and GP Putnam House – first publisher of the Bend Bulletin, a Bend mayor, and husband of Amelia Earhart). My favorite, is just to wander – check out the lovely Mirror Pond and Drake Park, pop into a few new or old shops, and grab a drink. If galleries and shopping are more your style, check out the numerous art galleries. Drake Park is a great place to relax and watch the local Bend-ites, or try playing a game called “Spot the California transplants”! ;)
12) Sun, Sounds & Suds
Head down to the Old Mill District to check out the Les Schwab Ampitheater. You’ll find free live music most Sundays during the summer, thanks to the Wells Fargo Summer Concerts series. Bring a blanket and your choice of Bend brews. Or if you have shopping on your mind, cross the footbridge over the river and listen to the music while you peruse the Old Mill Shops. If you need a bite before leaving town Jackson’s Corner is great for to go food (order the BLB!).
The Bend/Redmond airport is a 45 minute flight from Portland, OR on United, Alaska, Delta, etc. or a three hour drive from Portland, depending on weekend traffic. If you fly in, a rental car is suggested, as central Oregon lacks a mass transit system, and outdoor options are fairly spread out.
Airbnb or the Inn of the Seventh Mountain is good choice if you’re traveling with family or in a group. Right on the Deschutes River, The Inn is between Bend and Mount Bachelor.
Another recent favorite, McMenamins Old St. Francis School, is a perfect central location in downtown Bend.
Check out Visit Bend for tourist information and upcoming events.
Guidebooks: The only Oregon guidebook that I’ve seen that does justice to Central Oregon is Frommer’s Oregon.
What’s your recommendations for 36 hours in Bend?
Originally written in 2009, updated for 2018.
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