Winter Weekend – 48 Hours of Winter Fun

It’s a triple play when it comes to the perfect two-day winter stay in Central Oregon – starting and ending with three distinct experiences.


Based out of Sisters, after a pleasant night’s stay at FivePine Lodge, head to one of the town’s renowned bakeries to start the day. If you’re staying at Black Butte Ranch, brew up a cup and lay out some pastries in your vacation rental. After that, head to Hoodoo Ski Area to ski, ride or do a little innertubing down these Cascade slopes.

After a morning full of downhill runs, head back to Sisters for a late lunch or refreshments at the Three Creeks Brewing Company. If you haven’t been able to find time to see the latest movie, head next door to the Sisters Movie House, built inside a big red barn. If the slopes have gotten the best of you, there’s always the Shibui Spa at FivePine Lodge, just a two-minute walk from the theater and brew pub.

Day two is exploration day. It begins in Sisters with a relaxed cross-country ski tour on the Peterson Ridge trail system, a hike around nearby Suttle Lake or an amble along the Metolius River and into Camp Sherman. Try lunch at The Lodge at Suttle Lake.

Back in town, it’s time to troll the art galleries or hit the winter series of the Sisters Folk Festival, where you can find big acts in an intimate setting.

A family ice skating at Seventh Mountain Resort


If you’re launching from Bend, and staying at DoubleTree, Riverhouse on the Deschutes or the Hilton Garden Inn, try McKay Cottage or Sparrow Bakery before heading up for a day of alpine skiing.

Those wanting to be a bit closer to Mt. Bachelor will find a haven at Seventh Mountain Resort, five miles from downtown on the way to the ski area.

Legs a bit weary and ready to head back from the slopes, stop by The Row at Tetherow for apres ski or head right to town for a brew and a burger at either 10 Barrel Brewing Company or Cascade Lakes Brewing Co. Lodge.

Come evening, Bend has dozens of wonderful dining options such as the venerable Pine Tavern near Mirror Pond in the heart of the city.

After dinner, downtown has several music clubs, regular big-time music acts at the Tower Theatre, wine bars and places to simply sit back and relax after a long day on the mountain.

Or, an alternative itinerary for Bend would be to start off the day heading up Century Drive for cross-country skiing at one of the designated Sno-Parks, sledding at Wanoga Sno-Park or dog sledding with Trail of Dreams at Mt. Bachelor.

Back in town, explore the shopping downtown or in the Old Mill District. The dinner fare in town runs from Middle Eastern, to Far Eastern to Pacific Northwest and Western. In any case there are top-notch restaurants for every whim.

The Village at Sunriver Shopping


A third two-day excursion starts in Sunriver, with its wide variety of accommodations from lodge rooms and condos to rental homes. In winter, Sunriver is like being in a classic European alpine mountain community – small enough to walk everywhere yet replete with a central shopping and restaurant village.

The drive to Mt. Bachelor from Sunriver is short. When your legs can’t take any more on the mountain, head back to Sunriver Resort, where there’s Sage Springs Spa to minister aches and pains, Sunriver Brewing Company for conviviality and several excellent dining choices at the Lodge and in The Village at Sunriver.

Day two in Sunriver starts with a leisurely breakfast at Sintra before heading up to Edison Butte for a cross-country ski tour. By the way, dogs are welcome at Edison Butte.
Ending the tour with a picnic lunch on the snow is a fitting finale to two wonderful Central Oregon days.

The Hub – Redmond

Centrally located in the High Desert, Redmond is a community rejuvenated with upscale restaurants, a growing brewpub scene, ample lodging, vibrant parks and a bustling downtown district.

Through its music events, parades, farmers’ markets, fairs and festivals, Redmond offers visitors a true slice of Americana.

Nestled in Redmond’s backyard, Smith Rock State Park’s sheer, umber-colored cliffs is top destination to the north, attracting the worlds best rock climbers in addition to sight seers, mountain bikers and hikers.

Juniper Golf Club is one of  the premier courses in Oregon, with panoramic views of Mt. Bachelor, Broken Top, the Three Sisters, Mt. Washington and more. A true championship course designed by esteemed golf course architect John Harbottle, Juniper has repeatedly been a U.S. Amateur qualifying site as well as frequent host of the prestigious Oregon Open.

Strategically located at the hub of the tri-county area (hence the town’s moniker of The Hub) the Deschutes Fair & Expo Center plays host to a wide range of events, including concerts, sporting events, auto shows, trade shows, weddings, rodeos and more. The venue offers spectacular panoramic views of the Cascades, meticulously manicured grounds and more than 100 acres of parking.

Redmond is also home to Roberts Field, our regional airport that features direct flights to several hubs: Portland, Seattle, Los Angeles, San Francisco, Phoenix, Salt Lake City and Denver.

Welcome to Redmond, Oregon Sign

Must see: The Deschutes County Fair & Rodeo or the display of hundreds of flags in Flag City, USA.

Must do: Walk Redmond’s downtown antique district and relax with a brew at 7th Street Brew House. In the winter, enjoy outdoor ice skating.

Central Oregon’s Tax-Free Shopping Means You Won’t Leave Empty Handed

If you loved your vacation so much you want to take a piece of Central Oregon home with you, or you just want to take advantage of our tax-free shopping, we’ve got you covered with big-box stores and cute, locally-owned boutique shops.

The Village at Sunriver offers a relaxed atmosphere where you can get gifts for people back home or stock up on everything you need for your new favorite hobby. You can grab outdoor gear at Sunriver Sports, 4 Seasons Recreational Outfitters or stop by The Lazy Daisy for unique gifts, women’s accessories, seasonal merchandise and beautiful home decor.

If you’d rather rent, you can get the whole family set up with gear for Mt. Bachelor or riding bikes around town at various sports shops.

In Bend you’ll have the opportunity to stroll through quiet streets downtown and shop for quality clothing at our local boutiques such as Hot Box Betty and Cascade Cottons.

If you need a midday pick-me-up, stop in at Goody’s for a special treat.

On the east side of town at The Bend Factory Stores, you can get great deals on brands you love like Nike, Pendleton, Columbia and Coach.

Bend’s Old Mill District is about as distinct as it gets with our iconic stacks towering high above and iconic stores like Gap, Victoria’s Secret, American Eagle and REI.

From big name stores you’d expect in big cities to unique boutiques with small town charm, you’ll find a wide variety of shopping here on the High Desert; and plenty of restaurants to fuel your fun for hours on end!

Central Oregon Holidays are Happy at Historic Old Mill District

The Old Mill District is a year-round destination for shopping, dining and recreation – but when the holidays roll around, the historic area becomes a one-stop spot to truly embrace the season.

The Holiday Happenings kick off around 10 a.m. on Black Friday (Nov. 24th) when Santa arrives at the Les Schwab Amphitheater via Air Link helicopter – it’s truly a grand entrance for the big fella that the kids will want to see.

He’s here to check out the expanded SantaLand located in the space behind Athleta on the north end of the district. Santa plans to stop by Friday through Sunday to get up-to-the-minute lists from the Central Oregon kids and visitors.

Additionally, you can enjoy complimentary carriage rides on weekends leading up to Christmas with donations and tips going to benefit Kids Center, a local non-profit that helps prevent child abuse.

carriage ride-omd-shops

While you’re out shopping, take the opportunity to stop by the Gap, American Eagle and REI, take the opportunity to stop by the Tree of Joy at SantaLand. There you’ll find that children in need have written their name and ideal gift on a piece of paper and attached it to the tree. All you have to do is grab a name and return with the unwrapped gift. Hours are Friday through Sunday 11-5, November 24th through December 17th.

OMD Event Photos 095

Carolers from local school choirs and other groups will fill the Old Mill with the sounds of the season throughout the holidays, certainly making spirits bright.

Since shopping is pert near a combat sport during the holidays, be sure to take some time to replenish your fluids with a cocktail at Level 2 (or, if you’re with the kids, Red Robin has a full bar as well) or hot cocoa at Strictly Organic Coffee. Grab some sustenance for the endeavor at Flatbread Neopolitan Pizzeria, or, if it’s really chilly out and you want to transport yourself to someplace much warmer, give in to your imagination with a meal at Kona Mix Plate.

Central Oregon Ready for Busy Holiday Shopping Season

Photo: Talia Galvin
Photo: Talia Galvin

Central Oregon is home to dozens of small businesses and boutique shops that help give the region character, personality and a sense of place that resonates with locals and visitors alike. Yes, we’re known for our abundant outdoor adventure possibilities, but there is certainly no shortage of shopping here.

Downtown Bend is a hub for cute little brick and mortar shops including Cascade Cottons, which has the “must have” Bend and Central Oregon-themed shirts, sweatshirts and caps for yourself or for the dog sitter stuck back home while your out here having some fun.

Retail clothing photo by Jill Rosell in Bend, Oregon

Other shops like Cowgirl Cash (vintage, chic western wear for women) and Hot Box Betty (urban style in our small little mountain town) might just have that perfect little something to treat yourself to on your holiday vacation. And, of course, there’s always the gift of chocolate from local chocolatier Goody’s. 

Talia Galvin
Talia Galvin

You’ll find some great toys – including you know, the thick wooden, old-school toys you had as a kid – at Leapin’ Lizards and there’s some great gear for the cyclist in your life at The Hub Cyclery (which also has a couple of beers on tap at all times should the mood strike you during your shopping spree.) Need XC skis or winter gear? Check out Powder House or Pine Mountain Sports. If you plan on spending more than a few hours downtown, or want to arrange your shopping to end around dinner time, there’s plenty of great local restaurants downtown. Check out The Brickhouse for an awesome happy hour that includes brick oven pizza, bay shrimp cocktail, beef carpaccio and more.

first friday at Hub

Beyond downtown, you can find that perfect outfit at Lost Season Supply Co. fine linens and upscale home decor at Nicole Michelle and all the Oregon Ducks gear you could possibly want at The Duck Store.

Bend’s Old Mill District has the big box stores everyone loves, but it’s also home to several local shops that are looking forward to the holiday season, including Nashelle Jewelers, Savory Spice Shop and Saxon’s Fine Jewelers.  You can also take a break from the chaos with a movie at Regal Old Mill Cinema or by stopping by Hola! for a bite to eat. There’s plenty of Holiday Happenings in the Old Mill as well to make your shopping experience even more festive.


The shopping isn’t limited to Bend. You’ll also find cute boutique shops in The Village at Sunriver like Tumbleweed Toys, The Wooden Jewel and The Lazy Daisy clothing and accessories store. Get your gear fix there at Sunriver Sports, Village Bike & Ski or 4 Seasons Recreational Outfitters. Downtown Redmond is an antiques lover’s dream and downtown Sisters has cute western-themed shops that sell everything from unique quilting patterns to rare Oregon wine.

With so many options, it’ll be easy for you to crank out the Christmas shopping in one fell swoop so you can refocus your holidays toward something fun (like take a hike, hit up the slopes of Mt. Bachelor, take a snowmobile adventure or just snuggle in front of the fireplace in your room.)

(Guys, here’s the link you need: Great places to catch a game and grab a beer while the women are out shopping. You’re welcome.)

Downtown Redmond, Oregon

Central Oregon Campgrounds: Tumalo State Park

outdoor project collab image

Tumalo State Park

Forested setting: Check. Gentle flowing river to cool off in: Check. Toilets: Check. Showers: Check. Access to amenities in town: Check, check and check.

Tumalo State Park is the state park in Bend’s backyard. It’s located outside the city limits but it’s just a couple of turns and a short, pretty drive from the middle of town. For locals, that means it’s the perfect place to get out into nature for a fun family staycation. For visitors, that means they can get out into nature but be close enough to restaurants, breweries, shopping and other comforts of home. Experience the city by day, sleep under the stars next to the Deschutes River by night. You can’t get much better than that.

You can read more about it and see some great photos from our Adventure Partners at the Outdoor Project.

Connecting with Culture – High Desert Heritage

The Tower Theatre exterior in Downtown Bend, Oregon

Over the past two decades, Central Oregon’s communities have embraced the arts and made them an integral part of local life as well as an attraction for visitors. A walk through downtown Bend and the Old Mill District during one of the first Fridays of the month says it all. Paintings, sculptures and photography are on display in galleries, retail shops, offices and on sidewalks.

first friday at Hub
First Friday at The Hub Cyclery in downtown Bend

Throngs of people turn out no matter what the weather brings. Musicians on the streets and in the shops enhance the festive atmosphere. Art in the High Desert, a juried outdoor art show in August, is also a great local place to see world-class art.

People at outdoor art festival in Bend, Oregon

Beyond Bend’s First Friday Art Walks, summer and fall street festivals in the region feature fantastic works of art. Notably, the Sisters Outdoor Quilt Show has become an internationally famous event, attracting quilt makers from around the globe to show off their works outdoors throughout the town. The quilt show also includes seminars and workshops for quilters.

Sisters Outdoor Quilt Show Poster

On permanent display in the art scene, The Museum at Warm Springs in the town of the same name features one of the finest collections of Native American art and artifacts in the West. Handcrafted tribal treasures here include Patlapa, basket hats worn for ceremonies such as root, salmon and huckleberry feasts, and Sahaptin, painted rawhide cases which the Columbia Plateau people used throughout history for storage, packing and trading. Make this part of any of your Central Oregon cultural itineraries.

Museum at Warm Springs_4x6

Focusing on the flora, fauna and pioneer history of Central Oregon, the High Desert Museum south of Bend combines indoor dioramas, outdoor displays featuring birds of prey and live demonstrations of everyday pioneer life. A must-stop for families, the museum is also noted for presenting the best in contemporary landscape painting and photography.

Hawk in flight during show at High Desert Museum in Bend, Oregon

Moving from art to music, Central Oregon runs the gamut. For big-concert lovers, the Les Schwab Amphitheater along the Deschutes River in Bend presents national and international acts.

The Athletic Club of Bend also showcases top-name acts for its summer series of evening outdoor concerts. Redmond hosts a summer concert series as well, featuring well-established and up-and-coming regional musicians. A quick check of the local media when in Central Oregon reveals a lively music scene at local clubs year-round.

Folk music is alive not only at local clubs but at outdoor events such as the regular Pickin’ and Paddlin’ concerts on the lawn at Tumalo Creek Kayak and Canoe in Bend’s Old Mill District.

Pickin' & Paddlin at Tumalo Creek Kayak and Canoe

The center stage of folk music in Central Oregon is the annual Sisters Folk Festival, which deftly combines big-name acts with neophytes to the scene. Held September 5-7, the event features a number of indoor and outdoor venues throughout Sisters.

Classical music lovers should plan to visit in August during the Sunriver Music Festival. The venue is Sunriver Resort’s dramatic, historic, giant-log-beamed Great Hall, which hosts eight concerts from classical pops to piano.

While in Sunriver, take an educational jaunt to the Oregon Observatory and Sunriver Nature Center for constellations and owls.

Exterior of building at sunset in Sunriver, Oregon

Jazz fans can enjoy the Jazz at The Oxford series that runs fall through spring at the Oxford Hotel in Bend. And there’s the regular Jazz at Joe’s series that takes place at Bend’s Community Theater of the Cascades (CTC).

When not hosting music events, CTC offers a full schedule of dramas, comedies and musicals. So, too, with Bend’s 2nd Street Theater.

Offering its own mix of theater, film, music and lectures, the historic Tower Theatre is the crown jewel of downtown Bend. The theater also serves as the host location during the annual BendFilm Festival weekend that celebrates independent film and filmmakers. A new free, guided walk of downtown Bend is available whenever you want. Just download the new Bend Heritage Walk app at, and discover the colorful past of this frontier boomtown through its oldest buildings.

Northwest Crossing Saturday Farmers Market

And as the region’s creative community expands and evolves, so too does its farmers markets. Bend hosts three distinct markets from May until October—one in the heart of downtown, one on the grounds of St. Charles Medical Center and a third in Bend’s NorthWest Crossing neighborhood. Redmond holds a regular Thursday evening farmers market. All of these markets, taken together, promote Central Oregon’s farm-to-table culture and is the perfect place to stock up for a picnic.

While on an agricultural theme, try Maragas Winery’s old-fashioned annual grape crush in September. Purple hands are the signs of a true vintner. Chef Bette Fraser also offers culinary tours and classes through her Well Traveled Fork enterprise.

With its diversity of theaters, museums, art galleries and concert venues, Central Oregon is the place for a diverse cultural scene with a spectacular backdrop.

Shopping Central Oregon’s Malls and Collections

Old Mill District

Bend’s Old Mill District is its own small town of shops. Stretching along the bank of the Deschutes River, this revitalized historic site incorporates vintage brick buildings into a beautiful promenade with a popular collection of shops. Major retailers include Victoria’s Secret, REI, Coldwater Creek, Banana Republic and The Gap and local favorite Saxon’s Fine Jewelers.

With so much shopping to do here, you’ll need to stay energized with a stop for lunch, a local microbrew, cocktail, or dinner. At Greg’s Grill, Pastini Pastaria, Anthony’s and Level 2 in the Old Mill District, bask on the patios with gorgeous views of the Cascade Mountains over a tranquil stretch of the Deschutes River.

Head to the Ticket Mill for concert tickets, gift certificates, pint glasses, postcards, posters or check out binoculars and a birding list for viewing along this stunning avian migratory corridor.

must-have: The perfect dress that’s great over a bathing suit and can go straight to drinks and dinner on the patio.

Bend Factory Stores

At the south end of town lies one of Bend’s biggest secrets. The Bend Factory Stores have everything from sportswear and formal wear to children’s wear and home furnishings. For those who love a deal, the Bend Factory Stores has a Nike and a Columbia Sportswear outlet to name just a couple. Other stores in the outlet include The Coach Factory Store, Eddie Bauer Outlet, Izod, Pendleton Outlet and Pearl iZumi.

must-have: A head-to-toe high-tech ensemble that keeps you smiling and comfy under our true-blue summer skies or on snowy adventures – all at a reasonable price.

Bend River Promenade

The long-established Bend River Promenade Mall on Third Street is a hub of shopping variety in Bend. This shopping center is home to many of the trusted brands we grew up with, such as Macy’s, Kohl’s and T.J. Maxx. The Duck Store is just across the street for University of Oregon Duck gear and accessories.

must-have: A new pair of polarized sunglasses, because we have 300 days of sun a year, and even less rain than San Diego.

Cascade Village Shopping Center

The Cascade Village Shopping Center is located on the north edge of town. Here you’ll find many larger format stores including Trader Joe’s, Target, The Home Depot, Best Buy, Ross, Dick’s Sporting Goods and Famous Footwear.

must-have: Crunchy and delicious organic snacks for your trip up to the mountains, and gear that will keep you happy while you’re there, no matter the season.

A Shopper’s Dream

Boutiques & Gear

Imagine Frye boots, Coach handbags, Keen eco-flats and Salomon ski boots—without sales tax.

Visiting a new destination is about discovering new landscapes, people and lifestyles, and letting all that inspire you, right down to your personal style. Central Oregon has a relaxed, mountain-chic aesthetic that extends from fashionable clothes for town to high-performance sportswear and gear for the outdoors. You’ll want to take our style home with you. Fortunately, our region offers a range of retail variety, from small one-of-a kind boutiques to large chains and everything in between. Apparel to footwear, gifts to jewelry, locally made products to imports – there’s something for every shopper. Don’t forget, there’s no sales tax in Oregon.

Boutique Experience

For the small boutique experience, shop  The Village at Sunriverdowntown Bend, downtown Sisters, and downtown Redmond. Each of these locations offers a broad mix of shops with friendly shopkeepers offering highly personalized service. The shops lining the streets are woven among a blend of irresistible venues where you can dine and drink along the way.

The Village at Sunriver

This exceptional shopping experience, with boutiques, art galleries and sporting goods stores, is the place to go for whatever you need to make your visit that much more fun and interesting.

Browse original, handcrafted gifts and fine art from more than 30 local artists. Since you’re here to relax, get in touch with your crafty side with knitting and beading supplies. Have fun at the toy store or linger in the bookstore, perusing the perfect tome for your visit: fiction, non-fiction, mystery, or a local guide book. Rent a moped or stock up on fly-fishing equipment. Take home items unique to Oregon, and don’t forget some special treats for your pet.

The Pavilion at the Village at Sunriver in Central Oregon

After you’ve shopped ’til you’ve dropped, kick back at one of many distinctive dining venues that run the gamut from bistros to breweries and bakeries.

must-have: Oregon berry gourmet jams and syrups made from the renowned fruit of Oregon: marionberry, loganberry, black raspberry, red raspberry, wild huckleberry, blueberry, wild blackberry and Bandon cranberry.

Downtown Bend

There’s fashion, furniture, jewelry, art galleries, as well as plenty of restaurants, breweries, coffeehouses, ice cream shops and old-fashioned candy stores to keep you going. As you shop, you’ll enjoy strolling among charming brick buildings that date back to the early 1900s. Today the shopping scene is as vibrant as it was even in Bend’s early days as a booming timber town.

The Tower Theatre exterior in Downtown Bend, Oregon

Keep it local with Oregon Body & Bath. Here you’ll find some of the best products that Oregon has to offer, so you can surround yourself with the spirit of our state even after you’ve returned home. Don’t forget to stop in The Oregon Store, where you’ll find the best of Oregon-made goods: including Pendleton blankets made especially for Ducks and Beavers fans.

must-have: Pendleton Woolen Mills blankets and pillows add personality to any home. Accent a bed or sofa with these beautiful and functional items. This famous mill’s designs will energize a room or favorite chair, incorporating bold colors and patterns inspired by Native American traditions.

Cascade Cottons captures the character of Bend with fashionable and fun T-shirts, hoodies, fleece and hats sporting Bend, Mt. Bachelor, and Central Oregon logos. Proclaim your love for beer, the outdoors and all things Bend with casual apparel for the entire family.

must-have: The T-shirt that puts the Bend spin on the movie Star Wars, emblazoned with the phrase, “May the forest be with you!”

Cowgirl Cash is Bend’s boutique for used cowboy boots, belt buckles and jeans. Women from all over the world have come to love Hot Box Betty, and the shop’s personal styling expertise. Every piece of clothing and fashion accessory is selected with an eye for the latest trends that also fit the Bend lifestyle. In your search for the perfect collection of outfits for your dream closet, stop here for sensational pieces, and where the emphasis is always on service, service, and service.

must-have: Leather belts, cuffs, and handbags handmade from fine Italian leather in sumptuous saturated color. Exposed stitching imparts an artisanal organic quality. High-end denims with impeccable fit, finish, feel and originality and eco-chic yoga-inspired pieces. And, even the “world’s most comfortable thong.”

Celebrating a special occasion during your visit? Head down Newport Avenue to Donner Flower Shop, which has been doing fine floral arrangements and gifts here for more than a century.

Downtown Sisters

Downtown Sisters, Oregon

In Western-themed downtown Sisters, you’ll find more than Western wear. Stroll through the many art galleries and specialty shops. Find that undiscovered treasure in one of Sisters’ antique shops. Among the many specialty shops, you’ll find wonderful restaurants. Enjoy a scrumptious meal, taste some wine, grab an ice cream cone or just sit back and people watch.

must-have: Add some cowgirl (or cowboy) chic to your personal style with a great pair of boots and hat. These classics withstand all fashion fluctuations, are envied on city streets, or roughed up on our breathtaking trails. Need a wow-factor for your home? A rustic antler chandelier is it.

Downtown Redmond

Redmond is not only Central Oregon’s flight hub, this city offers retail with a view. It is also the place to shop for antiques. Cruise the emporiums on 6th Street and see what gems you can find. For contemporary tastes, there are unique home furnishing stores, hip clothing stores and cool coffee shops. Downtown Redmond is the unexpected jewel of retail therapy in Central Oregon.

must-have: Frontier-era glass apothecary jars, and early 20th-century cards and letters, handwritten by fountain pen and framed.

Downtown Redmond, Oregon