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By Emily Hunter | 11/15/2021 | Attractions, Family, Music, Outdoor Adventure, Performing Arts, Shopping, Ski & Snowboard, Things to Do, Wine

ROGUE VALLEY WINTER BUCKET LIST

Rogue Valley Winter Bucket List

When cool air is invited to the valley and the mountains become blanketed with snow, a world of possibilities are opened to locals and visitors alike.  Medford and its neighbors have a wealth of winter gems just waiting to be discovered and played in.

Southern Oregon and the Rogue Valley has your winter getaway ready and waiting! Whether you seek adventure in the mountains, fireside wine tasting or family friendly snow days,  Medford is your launchpad to checking off your winter bucket list. 

Conveniently located in the heart of the Rogue Valley, staying in Medford maximizes time away as everything in the valley is less than a 20 minute drive. 


Let’s get planning!


Mt. Ashland is the crown jewel of Southern Oregon, and you will feel like royalty as you cruise down the snow-clad slopes. With majestic views of the Siskiyou Mountain Range at every turn, become immersed in the valley’s natural beauty.

The mountain boasts 240 acres of skiing and riding terrain, in addition to four chair lifts which give access to 44 ski trails and open bowl skiing. If you don’t have your own equipment, Mt. Ashland features a full rental shop with ski and snowboard rentals, tuning and more so that you are fully prepared for your day.

The mountain provides terrain for skiers and riders of every ability. Learn the ropes at ski school or get some practice in on any of their green marked groomed runs. If you’re more advanced, explore steeper terrain in The Bowl or on any of their blue or black marked trails. If you would rather stay inside, Mt. Ashland has a Tudor-style lodge with food service, a bar and lounge. It’s the perfect place to relax after a day of skiing, or to sip a hot drink while you wait for the rest of your group to return from the mountain. Enjoy a hot meal, chat about the day’s adventures, and plan for tomorrow’s activities. Located just eight miles from I-5 near the Oregon-California border, leave your troubles behind and hit the slopes at Mt. Ashland!

You haven’t experienced a winter wonderland until you have seen Crater Lake. With an average of 42 feet of snow per year, the lake becomes a prime location for cross-country skiing and snowshoeing. The infamous Rim Drive that features a scenic look around the lake closes in the wintertime, and becomes a designated ski and snowshoe trail. Completing the entire circumnavigation of Crater Lake (31 miles) is an adventure for experienced winter adventurers and skiers, but does require more advanced knowledge and a backcountry permit. 

If you are looking for a less intense adventure, there are several beautiful trails to explore. One of the easiest and shortest ski trails in the park is the Mazama Loop, a 1.7-mile loop trail. The trail passes through the Mazama Campground and features views of the adjacent Annie Creek Canyon.

Whether you take the whole family out for some sledding, discover one of the trails, or trek Rim Drive, Crater Lake is the ultimate snow-filled paradise for winter family fun!

Downtown Medford Christmas

If you are looking for some good old family fun, this lights festival will overflow your holiday cup. This festively free event is held at Pear Blossom Park, with an array of booths and activities every member in your family will enjoy. 

Start the evening off watching a holiday tree lighting, and make your way over to the Lithia Lobby to compete in a coloring contest. After channeling your artistic abilities, it’s time for a fun photo with Santa himself! Find several other booths and activities to participate in around the park, including the infamous candy cane hunt, and enjoy live music performances throughout the evening.

The annual Providence Festival of Trees showcases stunning Christmas trees and displays decorated by local businesses, interior designers, florists and other talented people throughout the community. The festival has raised more than $11 million over the past 29 years to benefit the programs and services of Providence Medford Medical Center. 

This year, you are invited to tune in to the stunning displays virtually, while helping raise funds for critical programs that will support the community.

This modern family resort offers year-round service, but is most famous for it’s fabulous winter activities. Find all of the equipment you would need, from tubing to skiing and snowboarding, snowmobiling, and snowshoeing!

Your adventure begins on the ride up the hill, with their 470 foot “wonder carpet” conveyor lift that will take you to the top with ease. Tickets must be booked online, and will include unlimited rides within your three hour session, a tube, and 10% off if you purchase 4 or more tickets for your family. Enjoy multiple different lanes with fast tubes, glide more than 900 feet - the length of a football field - to the bottom, and take your family on a trip they’ll never forget!

Can’t get enough sledding? Neither can we! Table Mountain has a sweet sledding hill in the Cascade-Siskiyou National Monument. The hill is specifically designed for snow tubing and sledding, and offers a great spot for families to enjoy a day playing in the snow. The warming shelter is open during the winter months for you to relax and get dry between gliding down the hill, or enjoy a nice packed lunch with your family.

This sno-park is located near the summit of Mt. Ashland, and is the access point to the Mt. Ashland Southside (Grouse Gap) Nordic Trail System. This park is a great starting place for snowshoers and cross country skiers alike, offering a beginner system to get the hang of things before heading up the mountain for the more advanced trails. With quick access to the parking lot, and all of Mt. Ashland Ski Area’s rental equipment, dip your toes in the water this winter season to the joy of snowshoeing and skiing!

During the winter, one of the most notable wineries to visit is Kriselle Cellars. Enjoy one of their hand crafted, premium wines by their outdoor or indoor fire pits. Their expansive patio is a relaxing place to cozy up and spend an afternoon, or you might find that their tasting room overlooking the vineyard and ranch is more your fancy. Situated on a hill, find views of the valley and surrounding mountains no matter where you choose to indulge.

Southern Oregon snowmobile

The Lake of the Woods / Siskiyou Summit holds several different sno-parks just waiting for you to explore them. Each park offers different sets of activities for their specific landscape, such as cross country skiing, snowshoeing, and especially snowmobiling. 

One of the most notable places to snowmobile is Great Meadow Sno-Park, just 35 miles west of Klamath Falls. In the winter, you'll find over 165 miles of groomed trails for snowmobiling, cross-country skiing, and snowshoeing. Snowmobilers can cruise from Great Meadows to Diamond Lake and connect with a network of trails that crisscross Southern Oregon.

The snowmobile trails around Great Meadows are well-maintained. In a typical winter, 150-250 miles of trails are groomed every week. Douglas, Red Shasta, White firs and lodgepole pines shadow the trails around the meadow, with a sprinkling of aspen trees on the west end. This park is perfect for advanced and beginner riders alike, with large open spaces for learning and trails for the more experienced.

After a busy day of adventuring around the park, food and lodging are available at Lake of the Woods and Fish Lake resorts. Fill your hearts desire full of winter fun, and explore the endless possibilities of trails at Great Meadow Sno-Park!

Situated in the heart of downtown Ashland, this ice skating park is a family favorite. Equipped with all of the rentals you need, enjoy the crisp, outdoor air while skating and an array of concessions during your session. Neighboring Lithia Park and a tasty selection of restaurants nearby, you can enjoy an afternoon or evening of skating and dining in Ashland.

The park additionally offers hockey events, including stick and puck- a free play hockey session for all ages, private skating lessons and frozen tots for kiddos.

Located east of Medford and Grants Pass on Highway 140 (the route to Klamath Falls), this popular trout reservoir is an excellent place for ice fishing. January is often the best month to ice fish, when the lake is at 4,600 feet and has ice around 6-24 inches thick. Besides book trout, Fish Lake also has rainbow fish, land-locked Chinook salmon and a hybrid species known as a tiger trout.

The latter species was planted strictly to reduce the numbers of nuisance fish found here, and they must be released while the other species are available for harvest.

Start your visit near the resort, which is typically open Friday through Sunday during the winter season, and rent an ice auger to drill your hole. When you are finished with a successful trip of fishing, the resort also serves hot food and drinks to warm you up before your trip back home.

Whether you ride a Polaris, Arctic Cat, Yamaha, or Ski-Doo, Union Creek Resort is your one-stop for outdoor winter snowmobile adventure. The resort is your headquarters for 150 miles of well-groomed, uncluttered snowmobile trails packed with snow-laden trees, open meadows, deep snow and pristine vistas.

The magnificent scenery of this winter wonderland provides for a truly awesome experience. With plenty of room to get out and ride, this remote snowy region creates a perfect winter getaway for visitors and locals alike.

Craterian Theater

Located in the heart of downtown Medford, The Craterian Theater at the Collier Center for Performing Arts is the perfect place to cozy up and enjoy a performance you will never forget. The state-of-the-art theater hosts several different performances and plays, listed and updated on our event calendar. Enjoy a showing of Jake Shimabukuro’s Christmas in Hawaii, The Christmas Messiah, or a Celtic Christmas to celebrate the holidays. After the performance, grab a bite to eat at one of the eateries downtown, and end the night with a full stomach and heart, marveling at the lights and trees.

Medford Brews


After your showing at the Craterian Theater, you can also try out one of the many incredible breweries nestled in downtown Medford. Just a block down the road lives Portal Brewing Company, an intimate, brick-lined brewpub serving inventive house-label ales & eclectic comfort food. Grab a drink and a snack or two, and stay cozy inside this homey pub.

Just a bit farther of a walk you’ll find 4 Daughters Irish Pub. This large 2-story bar & restaurant comes equipped with old-world decor, live music, Irish & American pub grub and fantastic brews. Head on up the stairs to sit in their lounge area, and make yourself at home at this local brewery.


Kick off the winter lights festival with the annual candy cane hunt! After you complete your search around the park, make your way over to the Lithia Lobby to compete in a coloring contest. You can also take a photo with Santa, and discover several other booths and activities to participate in around the park. You won’t want to miss the live music performances throughout the evening, and the fireworks show at the end!

Come enjoy the beauty of kites freely filling the sky at the Winter Kite Festival at Lake of the Woods! Held this year February 12-14, the kites begin flying at the beginning of the weekend, and continue all day Saturday and Sunday until the early afternoon.

After taking in the sights, enjoy some pizza to-go from the Marina, or order some delicious food from the Lodge Restaurant.

A fabulous staple of the region, RoxyAnn Peak has one of the best views of the Rogue Valley. The beautiful landscape of the mountain grows golden grasses and scrub oaks, better known as mistletoe.

Take a leisurely hike around the peak, with trails for beginners, intermediate and advanced hiking and biking. Pick mistletoe for decorations, or admire it along the trails, and celebrate the holiday season with the crisp outdoor air and panoramic views!

The Village at Medford Center, downtown shopping, things to do in medford, holiday lights, christmas lights

Prep for the holidays and shop at some of the best local boutiques, gift shops and marketplaces in the Heart of the Rogue Valley. Shop for your dearest green-thumb at Bumble & Wren, a host to a hand-picked selection of plants, quality garden tools, wonderful gifts, and boutique home and outdoor accessories.

For your favorite antique lover, consider The RetroWormhole. Filled with posters, records, figurines and more, find a fun stocking stuffer or dream gift for your loved ones!

From the Village at the Medford Center, to the several boutiques nearby, checking off your gift list will not be difficult when you shop in downtown Medford!

Board a traditional 1920’s style trolley for a guided tour of Medford, and see the dazzling holiday lights around town! Begin with a cup of delicious hot chocolate at the iconic Harry and David Country Village, and take in the sights from the comfort of your seat and while heading towards East Medford.

Marvel at all the holiday lights that decorate the town and its landmarks, including Candy Cane Lane and Cherry Lane, and stretch your legs with a stroll around Greystone Court. Snap photos along the way of the gorgeous holiday displays, and enjoy a festively fabulous time singing carols as you fill up on holiday cheer with your loved ones.

What better way to kick off the holiday season than to marvel at gingerbread creations made by locals around the valley? Support the Craterian Theater at one of the Rogue Valley’s most unique benefit auctions and favorite holiday celebrations. Walk through the theater and marvel at the many tall, complex and probably delicious creations. 

Proceeds from the multi-day event make it possible for the Craterian to bring national and international performing artists to the community and to provide our stage as a one-of-a-kind resource for countless organizations and individuals.

Southern Oregon’s largest holiday, artisan and craft fair is held annually right at the Jackson County Expo. Only a 15 minute drive from Medford, you can browse hand-made and direct sales crafts from all around the region- a perfect place to find a lovely gift on your friends or family’s wish lists.

With more than 170 artisan and craft vendors, you are sure to find a one-of-a-kind handmade gift or delectable treat to take home with you!

Just 15 minutes from downtown Medford, explore the quaint and historic town of Jacksonville. Their annual Victorian Christmas parade brings the entire community together to celebrate the season. With several floats, Christmas carols, and special guest Santa Claus, you are sure to enjoy ringing in the holiday at this parade.

After the parade, enjoy a warm meal at one of their many eateries, or shop for a gift at one of their downtown shops.




From hitting the slopes to drinking cocoa on a trolley, Medford is a grand host to an abundance of different activities. Fill your heart this holiday season with festive winter events, and explore what the Heart of the Rogue has to offer you this season!

DECEMBER
3
Comedy Club at the Rogue Regency Inn
Join in on the fun at Rogue Regency Inn's comedy club! Tonight, laugh until your stomach aches with Rick D'elia…
VISIT WEBSITE
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Community Cupids - Holiday Edition
Join us in making the holiday's brighter for our senior community! Community Cupids is back again and spreading joy to…
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December First Friday Art Walk!
First Friday Art Walk: December 3, 2021 5:00 p.m. - 7:00 p.m. Please visit gallery, studio, and artist websites for more information…
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Holiday Book Clearance Event
Fingers crossed! Plan to attend our first Book Clearance Event in over a year, this December. Shop for holiday gifts,…
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3
Letters to Santa
How excited would your child be to receive a letter from Santa Claus? Bring your child's letter and place it…
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3
Live Music at The Talent Club
This is a band of veteran musicians who have joined together to honor the music of Tom Petty. Each…
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Wine + Music Series
Sip wine and enjoy live music performed by The Roadsters!
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DECEMBER
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Candy Cane Hunt
Kick off the Winter Lights Festival at the annual Candy Cane Hunt!
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DECEMBER
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Christmas at the ffarm - Crater FFA Land Lab
Welcome to WhoVille! Ready to get your Christmas spirit on?! We're so excited to welcome you back to the Christmas At…
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4
Christmas Messiah with the Craterian Theater
The Rogue Valley Chorale presents the Christmas movement of George Frideric Handel’s masterpiece, Messiah, with a dramatic presentation featuring the…
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DECEMBER
4
Community Christmas
Join us for Community Christmas! The parade will begin at 5pm and the beautiful tree lighting will begin at 6pm.
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DECEMBER
4
Flag Football at U.S. Cellular
Join a fun team every Wednesday at 6:30pm and Saturday at 10am for some co-ed flag football! You do not…
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DECEMBER
4
Jacksonville's Victorian Christmas
Jacksonville, Oregon celebrates the holidays and our past with Victorian Christmas. We decorate the town all in natural greenery with…
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DECEMBER
4
Live Music at StoneRiver Vineyards
Sip wine and enjoy live music performed by Wild & Blue!
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DECEMBER
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Medford Cars and Coffee
A gathering EVERY Saturday morning (unless it's raining or snowing) of car enthusiasts. Room for over 125 cars. Starbucks on…
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DECEMBER
4
Poinsettia Saturdays
Our Annual Poinsettia Festival will feature a large poinsettia display, festive music, photo booth, candy guessing game, raffle ticket for…
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DECEMBER
4
Take your Picture with Father Christmas
On weekends between November 27th – December 19th you can take family pictures with Father Christmas and enjoy musical entertainment…
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DECEMBER
4
Victorian Christmas Tour
Experience a Victorian Christmas this holiday season at the historic 1873 Beekman House Museum, located at 470 E. California Street…
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DECEMBER
4
Winter Lights Festival
Join Medford Parks, Recreation and facilities staff for the Annual Winter Lights Festival in Pear Blossom Park. Bring the whole…
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DECEMBER
4
Winter Wine Club Release
For reservations, please call the tasting room at 541-776-2315 Option 1
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DECEMBER
5
Corner Boy's perform at Oberson's!
Traditional Irish dance music, with an occasional song. Come see us at Oberon's in Ashland every Sunday 6–9pm!
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DECEMBER
7
Drive-by Live Nativity - Christmas at the ffarm
We want to give back to the community that gives so much to us... So we are rounding up socks…
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DECEMBER
7
Rogue Valley Growers and Crafters Indoor Winter Market
The Indoor Winter Market is open each Tuesday from December 7, 2021 through February 22, 2022. We're located at the…
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DECEMBER
9
Ghostlight Karaoke hosted by John Wing
We have a stage, we have a microphone... All we are missing is you! Choose your favorite songs to serenade your…
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DECEMBER
9
Winter Wreath Workshop
Join Freckled Fleurs for an evening filled with crafting a wreath full of unique textures, classic holiday greens, and fun…
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DECEMBER
10
Comedy Club at the Rogue Regency Inn
Join in on the fun at Rogue Regency Inn's comedy club! Tonight, laugh until your stomach aches with Tobe Hixx…
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DECEMBER
10
Holiday BrewPop and SeltzerFest
Join us for the FIRST EVER Holiday BrewPop Events @ The Expo! November features over 24 micro taps and…
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DECEMBER
10
The Nutcracker presented by Studio Roxander
Don't miss Studio Roxander's return to the stage with this beloved holiday tradition! The production will feature the students of…
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DECEMBER
10
Tutunov Piano Series presents: Angela Cheng and Alvin Chow
Angela Cheng and Alvin Chow will be the featured guest pianists, during the December concert of the 10th Anniversary Season…
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DECEMBER
10
Tutunov Piano Series presents: Angela Cheng and Alvin Chow
Angela Cheng and Alvin Chow will be the featured guest pianists, during the December concert of the 10th Anniversary Season…
VISIT WEBSITE
DECEMBER
11
Applegate Holiday Market
Come join us for our first annual Christmas market. The first European style Christmas market in Southern Oregon! We will…
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DECEMBER
11
Christmas at the ffarm - Crater FFA Land Lab
Welcome to WhoVille! Ready to get your Christmas spirit on?! We're so excited to welcome you back to the Christmas…
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DECEMBER
11
Disney's Beauty and the Beast - Presented by TMTO
"Be Our Guest!" The Academy Award-winning film comes to life on stage in this romantic and beloved take on the…
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DECEMBER
11
Live Music at StoneRiver Vineyards
Sip wine and enjoy live music performed by Just a Duo!
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DECEMBER
12
Aurora Vines at The Rogue Grape
David from Aurora Vines will be at The Rogue Grape on Wednesday pouring complimentary samples of their Tempranillo, Viognier and…
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DECEMBER
12
The Sounds of the Season
The Rogue Valley Symphonic Band presents The Sounds of the Season. Holiday Music from Around the World.
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DECEMBER
17
Christmas Lights and Cocoa
Tour will offer so much luminous holiday razzle-dazzle that you may want to wear shades! Take a driving tour and…
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DECEMBER
17
Comedy Club at the Rogue Regency Inn
Join in on the fun at Rogue Regency Inn's comedy club! Tonight, laugh until your stomach aches with Tommy Savitt…
VISIT WEBSITE
DECEMBER
18
Live Music at StoneRiver Vineyards
Enjoy live music performed by Ambrose & Galfano at StoneRiver Vineyards!
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DECEMBER
18
Ugly Sweater Party @ The Rocky Tonk
Come join us for a Ugly Sweater Christmas party at the Rocky Tonk!
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DECEMBER
18
Wrap It Up Family Christmas Event
Bring your children ages 6 weeks - 5th grade for a fun Christmas event while you sneak down to the…
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DECEMBER
19
Gnome Christmas
Gnome Christmas - $45 ea includes all supplies and 2 drinks! 16x20 Pre-sketched canvas - ok for ages 14 and up…
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CLICK HERE TO SEE ALL EVENTS
Attractions, Indoor Activities, Museums & History, Performing Arts, Rock Climbing, Sports Venues, Things to Do
Do you crave adventure, but you aren’t a fan of the cold? The Rogue Valley has several hidden gems and activities ready for you to enjoy this winter season. Explore all Medford has to offer, no heavy coat required.  Read More
Outdoor Activities, Outdoor Adventure, Things to Do, Water Adventures
Charming, mysterious and elegant waterfalls weave in-between, around and alongside the Rogue Valley’s mountains, forests and trails. Only an hour away (or less!) from numerous waterfalls, Medford is the heart of the Rogue and the launchpad for your waterfall journey. Whether you’re…  Read More
Attractions, Indoor Activities, Museums & History, Performing Arts, Rock Climbing, Sports Venues, Things to Do
Do you crave adventure, but you aren’t a fan of the cold? The Rogue Valley has several hidden gems and activities ready for you to enjoy this winter season. Explore all Medford has to offer, no heavy coat required.  Read More
Outdoor Activities, Outdoor Adventure, Things to Do, Water Adventures
Charming, mysterious and elegant waterfalls weave in-between, around and alongside the Rogue Valley’s mountains, forests and trails. Only an hour away (or less!) from numerous waterfalls, Medford is the heart of the Rogue and the launchpad for your waterfall journey. Whether you’re…  Read More
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