Guide to a Perfect 3-Day Weekend in Bend

Welcome to your “Guide to a Perfect 3-Day Weekend in Bend, Oregon!”  Bend is my current residence, & though part of me is loathe to write about it (because I don’t want more people finding out about it), I do realize it’s an awesome vacation destination ~ particularly if you love the OUTDOORS.  Bend is great for families, especially Sunriver; it’s great for pet-owners with all the open space & parks ~ & it’s even a great spot for a romantic getaway.  Once a logging town, Bend has turned into a craft beer & outdoor adventure mecca, & it’s one of the fastest growing cities in the country. 

As a new “local” in Bend, I’ll take you to all my favorite coffee shops, hiking trails, dog parks, quirky restaurants, & fantastic bars in this post…..

Visiting the Old Mill, an outdoor shopping & dining area that sits right on the Deschutes River, is a Bend MUST.

Author’s Note: In case you’re curious ~ here are some of my favorite brunch spots in Bend…or if you want to see the city in action: check out my Instagram Reel below of a great week in Bend, Oregon!

Guide to a Perfect 3-day Weekend in Bend

Where to Stay

First thing’s first in Bend: you need a place to stay for the weekend.  If you’ve got a big group, consider renting a house in Sunriver (about 25 minutes south of Bend) or via Airbnb.  Note that if you’re staying in Sunriver: you probably won’t come into Bend too often; it’s a good 25-minute drive.  This post focuses more on Bend, & below are my favorite Bend hotels.

Sunriver, about 25 minutes south of Bend, is the perfect choice for families with kids & big reunions ~ as you can rent large houses & condos down here. Plus, there are over 40 MILES of beautiful, paved bike trails here!!!

Great Upscale, Pet-Friendly Hotels in Bend:  Riverhouse on the Deschutes, Tetherow Lodge Hotel, & the Oxford Hotel Bend.  The Oxford is high-end & right downtown ~ you can walk to tons of restaurants & bars from here.  Tetherow sits high atop a bluff overlooking Tetherow Golf Course, with phenomenal mountain views.  Riverhouse has comfortable rooms & is set right on the Deschutes River, near the freeway.  For a more complete list of pet-friendly accommodations in Bend, click here.

Quirkiest, Most Unique Hotel in Bend:  McMenamins Old St. Francis School.  This is one of my favorite bar/hotels/movie theaters ANYWHERE!!!  Even if you don’t stay here: you MUST at least grab a drink, or bring a swimsuit & soak in their indoor hot tub.  Built in an old Catholic school, this rambling property has a boutique hotel, several quirky & fun bars/restaurants, a movie theater, & is right downtown.  Plus there’s a “secret,” speak-easy type bar hidden on property.  This place is AMAZING!!  GO!! (And there burger & tater tots are our running favorite in Bend…)

My friend, Jessica, soaking in McMenamin’s indoor hot tub, looking up to its open ceiling. Even if you’re not a hotel guest: you can still soak ~ just bring your ID to the front desk & bring a towel!

Friday Itinerary in Bend, Oregon

Okay: so you’ve made it to town, unpacked your bags, & maybe even had a drink at your hotel bar.  If you make it to town early enough, squeeze in a quick hike or bike ride!  For mountain biking, there’s nowhere better than Phil’s Trail, a massive complex of trails on the west side of town.  You could spend HOURS here!!  For a quick sunset hike in town: climb Pilot Butte, which stands right in the center of town & takes about 30 minutes to climb.  On top, you’ll have 365-degree views of Bend & all the surrounding mountains….

Pilot Butte is one of the best places in Bend to catch the sunset, with 365-degree mountain views…

Another good place to enjoy the sunset in Bend? On the Deschutes River, by the Old Mill ~ like our friend Karissa, pictured here.

Friday Itinerary Re-Cap

• 3PM = Check into your house or hotel. 
• 4PM = Rent a mountain bike & head to Phil’s Trail, or for killer sunset views & a short hike: head to Pilot Butte.
• 5:45PM = Catch the tail-end of happy hour & grab some food at anyone of these Bend classics: Crux Brewing (huge grassy lawn + pet-friendly), Evoke Winery (used to be called “Naked Winery” ~ drinks only, in the Old Mill district), 10 Barrel (east & west locations), Monkless Brewing (sunset views over the Deschutes River), or McMenamins St. Francis School.
• 9PM= My favorite spots in Bend for a nightcap are the outdoor cigar bar with fire pits at McMenamins (in the back parking lot, behind the hotel), Velvet Lounge, which is a quaint, cozy little place with amazing cocktails, or our new favorite: Dogwood Cocktail Cabin. There’s no better place to cozy up on a cool night than at romantic Dogwood ~ their cocktail list is unrivaled in Bend, & their few food selections are also very good (think: sliders + donut holes).
  

  Dogwood’s low lighting, phenomenal drink menu, & cozy setting make it one of the greatest nightcap spots in Bend.

Preview of coming attractions: if you want to hike to THIS view, be ready to get up early & head to Tam McArthur Trail!

Saturday Itinerary in Bend, Oregon

Saturday Itinerary

• 8AM = Grab coffee with the best view in town: Looney Bean Coffee, which sits right on the Deschutes!  Then take a stroll in neighboring Drake Park, which is set along beautiful Mirror Pond.
• 9AM = Get brunch!!  You have TONS of choices.  The two most popular brunch spots in Bend are Chow & McKay’s Cottage; both have cottage-vibes, & there’s ALWAYS a wait.  You can also try: The Lemon Tree downtown (French cafe vibes & DELISH food!!), & Jackson’s Corner, a local’s favorite.  For a full list of brunch choices in Bend: read this article.
• 11AM = Pick your outdoor activity: hiking, biking, rafting or kayaking!  Great hiking trails by town include Green Lakes, Six Lakes, & Tumalo Falls.  For mountain biking: head to Phil’s Trail ~ or with kids, check out Sunriver’s paved trails.  If you’ve got a dog, read my write-up on the best off-leash dog parks in Bend.  Walk or run along the Deschutes River Trail, with or without your pup!  In summer, head to Riverbend Park, where you can rent paddle boards or rafts ~ & launch right from the park.  Bend recently added a new whitewater park by the Old Mill District, & you can raft right down the “mini” rapids!  SOOO FUNN!!  There’s also a river wave to surf if you’ve got your board & wet suit.  In winter, ski or board at Mt. Bachelor, or rent cross-country skis & head to Wanoga Snow Park with your pups, or Virginia Meissner Snow Park for a pup-free experience. 
• 3PM = Grab a late lunch at hot spot Spork or uber-healthy Active Culture.  Or try lesser-known Global Fusion (yummy salmon tacos!!), right on Newport Ave.  Then get some R-E-S-T!!! 
• 7PM = Since Friday night was more relaxed ~ maybe you want to go more upscale tonight.  Try the BBQ Shrimp appetizer at Zydeco in downtown: the single-best dish I’ve had in Bend so far!!  For great brews & delicious comfort food, head to local’s favorite: Immersion Brewing: which has the best cobb salad in town!!!  I get it at LEAST twice a week.  Or if you’re feeling like Thai food, try Noi Thai (fancier) or Wild Rose (less fancy), both downtown.
• 10PM= For a night-cap tonight, try Brown Owl (next to Immersion Brewing).  For more of a “scene,” walk across the street to River Pig.  And if you’re looking for live music, check out quirky-cool Volcanic Theater Pub.

Here’s a list of my favorite places to paddle board by Bend ~ or read about my five favorite lakes that are about 20-30 minutes from town….

Grab coffee & a breakfast sandwich at the coffee house with the best view in town: Looney Bean. Their backyard has a large grass-area, adirondack chairs & picnic tables, & of course is pet-friendly.

Phil’s Trail is THE place in Bend to mountain bike. Budget at least two hours to ride dirt trails through the forest here.

My dog Dylan enjoying a cool respite on the easy Six Lakes Trail. Hiking options in Bend are E-N-D-L-E-S-S!!! Six Lakes Trail is on the Cascade Lakes Hwy, past Mt. Bachelor (about 40 minutes from Bend).

Green Lakes is the most popular hiking trail in Bend ~ but my vote for the prettiest is hands-down Tam McArthur Rim Trail, accessible via Sisters.

No matter what you’re doing in Bend: ALWAYS make sure you’re outside at sunset time!! This is another shot from atop Pilot Butte.

Volcanic Theater is one of the best spots to go in Bend for live music ~ we’ve even watched a Burlesque Show here!

What to Do on Sunday in Bend

Sunday Itinerary in Bend

• 8:30AM = You probably want to sleep in a bit after an action-packed Saturday.  If you loved Looney Bean, head back ~ or try one of the other umpteen-excellent coffee shops in town: Thump Coffee, Backporch Coffee Roasters on Newport, Strictly Organic downtown on Bond Street, or popular Sisters Coffee in the Old Mill.  Grab your coffee, then take a walk along the very popular Deschutes River Trail.
• 10AM = Have brunch at one of the spots listed above you didn’t try yesterday.  The earlier you get there ~ the shorter the wait. 
• 12PM = If you’re a golfer, make a tee time at cute Widgi Creek, or try your luck on a golf-board at beautiful Tetherow Golf Course, with its breath-taking mountain views.  If you’re headed back to Portland, stop off at Smith Rock outside of Madras for some rock-climbing & hiking: this is a STUNNING outdoor, natural area!!!  And dogs are welcome.  Even if you don’t enjoy hiking, great photos can be taken right from the parking lot.
• 3PM = Grab a massage at one of my two favorite massage places in town: Amazing Foot Spa in south Bend has a killer $40 full-body, fully-clothed massage, where they start by soaking your feet while giving you a scalp massage.  H-E-L-L-O!!!  Amazing.  For a more upscale experience with showers & an infrared sauna: try Anjou Spa on the west side.
• 4:30PM = Sunday afternoons are all about enjoying happy hour outside.  My favorite spots: 10 Barrel West Side, Crux Fermentation Project (huge grassy lawn + pet-friendly ~ but can be touristy), Avid Cider (locals-favorite), On Tap  (bomb outdoor food trucks & 20+ beer/ciders on tap) on the east side, or Bend Brewing Company ~ which has a large outdoor area & plenty of seating on the Deschutes River. Bend is known for its food truck scene: Podski (across from River Pig), The Bite (in Tumalo), & Midtown Yacht Club (east side of town), are all really popular spots that are kid & dog-friendly.

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  THE quintessential Bend shot of the Deschutes River Trail. Walking along this trail is a Bend MUST ~ I take Dylan down here at least once a week. The trail is so long (& on both sides of the river), that it rarely gets “crowded.”

  

  Hop on a golf-board (if you dare) at Tetherow Golf Course. Its hilltop position gives you panoramic mountain views towards the Sisters Mountains west of Bend.

  

  If you’ve got active dogs ~ take them to AMAZING off-leash dog parks like Pine Nursery (pictured) or Good Dog/Rimrock Trail (by Tetherow).

  

  If you’re driving back to Portland, Smith Rock is on your way home (via the Mt. Hood route). It’s just a 45-minute drive north of Bend, & the red rock views are to DIE for!! This photo was taken on the Misery Ridge hike.

  

  You haven’t really been to Bend until you’ve experienced at least ONE of its food trucks: pictured here is popular Podski, located off Colorado Ave.

  

  Best way to spend a Sunday afternoon in Bend?? Get outside & enjoy a beer with friends. This photo was taken at the 2019 Bend Brew Fest (which only happens once a year) ~ but you can drink outside at Crux, Bend Brewing Company, Avid Cider, 10 Barrel, On Tap, & many more places…

  

  Bend in winter.

Guide to a Perfect 3-Day Weekend in Bend

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