City to Cascades: A Perfect Weekend

Green Lakes

We have friends that pass through Bend all the time, and my boyfriend likes to joke that I must be getting paid by the Visitors Association because I give Bend the hard sell! I’ve lived all over the country and know how special this area is. My favorite three days in Central Oregon will highlight just that: the area’s good food, beer, wine, rivers, mountains, trails, festivals and more.


One of my favorite breakfast spots in Bend must be Jackson’s Corner. The cafe’s food is not only delicious, but primarily local and organic, the outdoor tables allow you to catch a bit of warmth from the morning sun, and the coffee, well, they know how to make a cup! I’d recommend the Pesto & Eggs (house-made Pesto!) or the Biscuts & Gravy (sausage from Redmond Smokehouse…mmmmmm).

From there the Old Mill District is just a hop, skip & a jump away. Pick up the Deschutes River trail right by Miller’s Landing Park and meander along Bend’s famous water-way. If you need to walk off breakfast I might suggest crossing the river on the Colorado Street bridge’s walkway and head upstream on the west side of the river.

Les Schwab Amphitheater

You will walk right through the Les Schwab Amphitheater and will see our new (in 2013) mural on both sides of the stage. Cross back to the east side of the river over the footbridge, it will lead you right into the heart of the Old Mill. I’m partial to the REI there in the iconic building, an old powerhouse for the mill that occupied the riverfront until recent times.

While Central Oregon’s beer industry is booming, our wineries and spirits deserve some attention as well. After a bit of shopping, load up the car and head for Maragas Winery  just past Terrebonne and practically in the shadow of Smith Rock State Park. Maragas was the first winery in Central Oregon; the microclimate is perfect for several different northern European varietals and hybrids. Grab a glass of their Malbec or maybe if it’s a warm day, their Poetic Pinot, a crisp and fruity white wine.

Wedding and music event center near Bend, Oregon

Next on the list is one of the area’s newer wineries, Faith, Hope, & Charity Vineyards. From their stunning vista of the Cascade Mountains (and their namesake Three Sisters: Faith, Hope, & Charity), the fertile valley is ideal for the cold-hardy grapes that blanket the rolling property. Sit in the beautiful little garden by the pond and enjoy a glass of Chardonnay or Frontenac.  Both Maragas and Faith, Hope & Charity are part of the newly formed Central Oregon Wine Trail.

Central Oregon Wine Trail

As long as you have a designated driver, the next stop on the tour is Bendistillery. Take a tour of the 24 acre farm and distillery while you sample their Crater Lake Gin (made from ingredients grown on the premises) or one of the four flavors of vodka.

It’s probably time for some dinner at this point! One of the hottest dining options in Bend has to be Zydeco. The Cajun/Southern Soul food menu offers some incredible options. Start with the Barbecue Shrimp and Southern Grit Cake before ordering the Shrimp Etoufee or more American classic, the Slow Roasted Pulled Pork Sandwich.

Zydeco Restaurant
Zydeco in Bend

Food coma achieved: time to rest up for Saturday, we’ll be heading to the mountains for some hiking, picnicking and more.


Central Oregon loves a good local product or service, so lets make breakfast this morning from some of the delicious options in town. Head to Galveston Avenue on the West side of town and pick up some bacon or house-made sausage from Primal Cuts Meat Market. Right next door is Paradise Produce where you can find all sorts of organic and local veggies and fruit for your meal.

Lava FlowThen swing by Backporch Coffee Roasters for some freshly roasted coffee beans or grab a cup to go, one more stop to make! It may be off the beaten path, but Central Oregon Locavore is the place to go if you like healthy and local products. Pick up a dozen farm fresh organic eggs and head home to make a truly Central Oregon meal.

I’m glad you ate your fill because it’s time to go on one of the most beautiful hikes in the Cascade Mountains. I know, i know, you just ate, but swing by Big O’ Bagels for a turkey club bagel sandwich to enjoy later for lunch.

It’s time to head to one of the more popular trails out there, the Green Lakes Trail, but there is a reason! The hike heads up to a stunning green/blue lake at the base of South Sister and Broken Top Mountains. The full effect needs to be experienced, and the hike up there isn’t half bad. You follow the charming little Fall Creek which has tons of splashy waterfalls to enjoy as you stop and catch your breath (you will gain over 1,000 feet in the 4.2 miles up).

An incredible lava flow comes into sight as you approach Green Lake. South Sister last erupted 2,000 years ago, so in geological time those rocks are quite young!

Just a little further, and you made it!

Paddling Green Lakes

One of my favorite visits to Green Lakes was while there was still some snow on the ground in the higher elevations. I took my packraft with me (a 6lb inflatable boat) to the lake and slid into the water from a snowy bank. I also had a beer with me that I stashed in a floating ice chuck in the lake for a tasty beverage later. Bringing a beer on a hike is always a good idea, especially since many Central Oregon breweries are canning now. (Worthy Brewing’s Prefunk is a great choice.)

Soaking tub at McMenamins in Bend, Oregon

If you are a bit tired and sore from the hike, head to the Old St. Francis School soaking pool at McMenamins in downtown Bend. The heated pool is garnished with colorful tile work, and with the open ceiling, is reminiscent of a Turkish Bath house. It is the perfect way to unwind after your trip to the mountains.

One final beer or two is in order from their back bar, O’Kanes. Sometimes referred to as the whisky or cigar bar, this little grotto has fire pits, outdoor seating and a selection of beverages ranging from their own beers and wines to whiskies. If you decide to order some food, try the Cajun Tots. Haven’t had a tot since grade school? These are much improved with cajun seasoning and are served with ranch dressing. You are welcome!

mcmenamins o'kanes fire


It’s a beautiful morning, fill that Hydroflask with some coffee, we’re going to the river for a morning paddle. Since the Deschutes River runs right through the middle of town and is fairly slow moving in spots, you can paddle up stream from Drake Park to the Colorado Street Bridge before turning around to float back. The city is quiet and the mountains glow on the horizon this time of morning.

big kayak

You’ve returned to the put-in at Drake park, time to put the boats away and grab bikes and head to breakfast. The Victorian Cafe or Chow would be my recommendations today. Both have incredible bloody Mary’s and the Victorian Cafe has an impressive selection of eggs Benedict.

Returning to the bikes, it’s time to check out one of the many festivals or fests that Bend has each year. One of my favorites is Art in the High Desert the last weekend in August. The show brings in over 100 professional artists from all over North America to the grassy banks of the river in the Old Mill District. I’ve gotten some amazing ceramics in year’s past, I’m positive you will find some art to bring home.

People at outdoor art festival in Bend, Oregon

Still have some energy? Might be nice to keep biking on the River Trail, multiple bridges across the river all for all kinds of different bike loops, it all depends on how far you want to go!

Time for a bite to eat, so bike on back over to Galveston Ave. and head to The Lot. The Lot is a food cart “pod” that’s been around for about a year…centered around a covered courtyard that serves…beer! Pouring from 16 taps, you can enjoy another local beer while trying food from one of the six food carts. I usually hit up Real Food Bistro or the Brown Owl. The Sandwich from The Brown Owl is particularly impressive (if you like fried chicken that is).

Goodlife Brewing outdoor garden area in Bend, Oregon

Lets work off some of that lunch by playing a little corn hole at Goodlife Brewing. Just a few blocks away, the brewery has a great grassy area with games, a fire pit and sometimes music. It’s a nice place to spend the afternoon while sipping.

Pilot Butte State Park in Bend, Oregon

It’s almost evening; a great place to watch the sunset over Central Oregon is Pilot Butte. Hop on your bike for the ride over to the East side of Bend. The extinct volcano rises 500 feet above town and provides a stunning view any time of day.

It’s getting late, but if you need one more bite to eat before calling it a day, head to Barrio in Downtown Bend. Their small tapas-style plates are great to share and everything goes well with either their Red or White Sangria.

Well, it’s been a whirlwind three days, but you have experienced why we all love it here so much!

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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