36 Hours in Bend, Oregon

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 since their population has almost doubled 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 five years has seen explosive growth. The upside was much needed retail development (Trader Joes, Old Mill district shopping, REI etc) and fantastic eateries to compliment Central Oregon’s already amazing outdoor pursuits. The downside is unfinished, vacant vacation home subdivisions and nation-leading unemployment rates. So help Bend out and throw them some tourism dollars!


6 p.m.

1) Downtown – On Foot

Start off your weekend by checking out downtown Bend, on foot. 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 locals, or try playing a game called “Spot the California transplants” ;)

8:30 p.m.

2) Not Your Typical Dinner & A Movie

One of McMenamins’ newest renovations, Old St. Francis School (700 NW Bond Street; 1-877-661-4228), is a one-stop shop for catching a $3 movie, pizza and McMenamins handcrafted ales. It’s one of the smallest McMenamin’s theater pubs though, so make sure to get there early. 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.


9 a.m.

3) Breakfast Time!

In paradise, the weekends aren’t for wasting, but you’ll need to fuel up for your action-packed day.  Head to Alpenglow Cafe (1133 NW Wall St #100; 541-383-767), one of Bend’s longer term residents. Alpenglow is known for using local food, (and their stellar pancakes). They even offer a $1,000 reward if you can find a can opener on-site. ;) There are so many new places popping up in Bend, that your best bet for the latest and greatest is to check out Foursquare and Yelp.

10:30 a.m.

4) Hiking, Kayaking, Rafting

You really can’t go wrong in choosing an outdoor activity in Central Oregon. For an easy one mile loop, check out Sparks Lake, 25 miles west of Bend. For a longer hike, try the Deschutes River Trail, that connects downtown to Benham Falls & Dillon Falls. 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 ($42). They also have a kayak tour along the Upper Deschutes river, pulling out just above Dillon Falls ($35).

4 p.m.

5) Brewery Hopping

Start out with a free brewery tour at Deschutes Brewery (901 SW Simpson Avenue; 541-385-8606), 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 Brewing Company (1019 NW Brooks St; 541-383-1599), near Drake Park. Overlooking Mirror Pond, the restaurant has fabulous burgers and beer (obviously). Every year more and more breweries open in Bend, so check out Visit Bend’s Ale Trail for the latest list.

8 p.m.

6) Stargazing

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 you’re less-inclined to be checking out real nightlife outdoors, head downtown to a few new wine bars or Bend Distillery (850 NW Brooks Street; 541-318-0200).


10 a.m.

7) Coffee

A newer Bend establishment, Strictly Organic Coffee (6 SW Bond Street; 541-330-6061) has outdoor seating, free wifi and a modest, but economic breakfast menu. Want something more filling? Check out Chow (1100 NW Newport Ave; 5417280256) on the west side. Another newcomer to the Bend breakfast scene, it’s a little spendier, but mighty good.

1 p.m.

8) 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.

The Basics

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.

The Inn of the Seventh Mountain (18575 SW Century Drive, 541-382-8711) 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 (700 NW Bond Street 1-877-661-4228), is a perfect central location in downtown Bend.

Check out Visit Bend for tourist information and watch their Twitter feed @TwisitBend for deals and upcoming events. @HackBend is also a good Twitter resource for local info.

Guidebooks: The only Oregon guidebook that I’ve seen that does justice to Central Oregon is Frommer’s Oregon.

What’s your favorite thing about Bend?


  • We definitely have some of the best breweries in the country! I love Worthy Brewing.

  • Thanks for the helpful article. I’m heading there mid September for my 10 year anniversary.

  • White water rafting on the Deschutes; especially Big Eddy, is a personal favorite. Families with young children should not be put off by this trip as Sun Country Tours offers a mild, escorted float trip.

    The High Desert Museum is also fun for families. Visit the small town of Sisters next door and feed the llamas at Ponderosa Lodge.

    I’m @Nancydbrown for all things travel-related. Oregon lover, too.