Winter Bucket List Header
By Emily Hunter | 11/15/2021 | Attractions, Family, Featured Articles, 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 have 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 the Heart of the Rogue, 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!

NOVEMBER
28
Black Friday Escape for Women @ Ravissant Cellars
Need a break from the chaos of cooking, shopping, or football? Take a deep breath and join us for a relaxing…
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NOVEMBER
28
Hansel & Gretel @ Camelot Theatre
For the Holidays, come and experience the magic of our newest original production, Hansel & Gretel, at Camelot! A Panto…
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NOVEMBER
28
Holiday Train Display
Enjoy the sights and sounds of holiday trains at the Rogue Valley Mall again this year from the Medford Garden…
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NOVEMBER
28
Jared Gutridge Duo @ DANCIN
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NOVEMBER
28
Jeff Kloetzel @ Dos Mariposas
Southern Oregon’s favorite singer-songwriter Jeff Kloetzel will bring his rhythmic guitar, soulful vocals and mixed bag of originals and favorites.…
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NOVEMBER
28
Mark Charles Hill @ Red Lily Vineyards
🍷 RED Friday 🍷 Skip the mall & bring your family to Red Lily Vineyards this Friday, November 28th, for delicious…
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NOVEMBER
28
Merry Market & Christmas Faire
Introducing the Holiday Event Series — three large-scale, family-friendly markets featuring 200+ curated vendors and thousands of eager holiday shoppers.…
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NOVEMBER
28
Nathan Stone @ Trium Wines
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NOVEMBER
28
Shakedown @ RoxyAnn Winery
ShakeDown is a Southern Oregon Classic Rock n Roll cover band that plays 70’s, 80’s to current classic rock tunes.…
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NOVEMBER
28
Tres Palomas @ Dunbar Farms
Tres Palomas is comprised of Mari Simone on vocals, Sean Chon on upright bass and Jason Wolverton on guitar, specializing…
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NOVEMBER
29
Ann Kelly & Mark Ross @ Dunbar Farms
Celebrate the synergy of Ann Kelly’s vocals and Mark Ross’s keys in an intimate, rich setting. Their performance blends jazz,…
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NOVEMBER
29
Charlee Prayers @ Remotion Wine
Stop by on tree lighting night for live music, mulled wine and hot chocolate!
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NOVEMBER
29
Christmas Tree Lighting @ Dunbar Farms
Join us as we light up our holiday tree on the covered porch. Bagpipe music will grace the ceremony and…
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NOVEMBER
29
Country Throwback @ Rocky Tonk Saloon
DJ Poppa will be throwing it back to the 80’s & 90’s playing all your favorites! Party starts @ 9pm!
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NOVEMBER
29
Friendsgiving @ Del Rio Vineyards
Join us for our Friendsgiving celebration from 11 a.m.-5 p.m. in our winery tank room. We'll have fun, games, and…
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NOVEMBER
29
Holiday Extravaganza @ The Expo
Join us for the 11th Annual Holiday Extravaganza festivities! Come and support your local businesses and artisans! We have over…
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NOVEMBER
29
Jared Gutridge @ Naumes Suncrest Winery
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NOVEMBER
29
Jen Ambrose @ StoneRiver Vineyards
MUSIC + FOOD + WINE Stop by StoneRiver this Saturday for an unforgettable evening featuring special guest JEN AMBROSE! Don’t…
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NOVEMBER
29
Local Vendor Fair @ Gold Rush Brewing
Experience the best of our community! We’ve got local makers, great food, fresh beer, cider, wine, and cocktails all day.
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NOVEMBER
29
Merry Market & Christmas Fair
More details to come.
NOVEMBER
29
Rogue Suspects @ Ravissant Cellars
We're excited to welcome Rogue Suspects back to Ravissant Cellars for the second time this month! Come enjoy the music…
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NOVEMBER
29
Santa Paws @ Edenvale Winery
Bring your pup (and your people!) for a festive photo with Santa among the beautifully decorated historic grounds of EdenVale…
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NOVEMBER
29
Tree Lighting Party @ Woolridge Creek Vineyard
Join us Saturday, November 29th for our inaugural tree lighting party! 🎄We can’t wait to share the holiday cheer with…
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NOVEMBER
29
Vista 222 Holiday Antiques Bazaar
Step inside Vista 222’s catering room and bridal suite for a holiday antique bazaar filled with character and charm. Explore…
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NOVEMBER
29
Wreath Making at Hanley Farm
Southern Oregon Historical Society will host its annual wreath making workshop—an opportunity to relax, forget the hustle and bustle, tap…
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NOVEMBER
30
Jeff Kloetzel @ RoxyAnn Winery
Join us at RoxyAnn Winery as we welcome Jeff Kloetzel with his soulful vocals and rhythmic guitar to the Tasting…
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NOVEMBER
30
Kitten Yoga @ Zen & Tonic
Relax, stretch, and get covered in kittens — truly the purrfect way to spend your Sunday! Hosted by the amazing Camren…
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NOVEMBER
30
Mike Whipple @ Woolridge Creek Vineyard
Enjoy wine, cheese, and live music at Wooldridge Creek Vineyard! No Cover Charge
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NOVEMBER
30
Music Bingo @ Dos Mariposas
It’s our first ever Music Bingo night at Dos Mariposas! Think you’ve got what it takes to name that tune and…
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NOVEMBER
30
Nick Garrett Powell @ Naumes Suncrest Winery
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NOVEMBER
30
Solo Sundays at Del Rio Vineyards
This November, join us for complimentary live music each Sunday from 3 - 5 p.m. in the comfort of our…
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DECEMBER
1
Trivia Night @ Jefferson Spirits
🗓️ When: Every Monday at 6:30 PM 📍 Where: Jefferson Spirits, 404 E Main St, Medford, OR 97501 Think you’re a trivia…
DECEMBER
2
Trivia Night at The Copper Plank
Join us for trivia Tuesdays at The Copper Plank! Come strain your brain and drink while you think. Round up…
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DECEMBER
4
American Crown Circus
The circus comes to Medford! Acrobats, high wire acts, clowns and more all at the Rogue Valley Mall December 4-7.
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DECEMBER
4
Christmas Cookie Decorating @ Padigan Wines
Intimidated by elaborate sugar cookies? Join our beginner-friendly Christmas sugar cookie decorating class! What you’ll get: - Six circle cookies and icing…
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DECEMBER
4
Ladies Night on Pint Rider @ Jefferson Spirits
One tour every Thursday – 6:30 to 8:30PM, Departing from Jefferson Spirits (Just the BIG bike out front, you…
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DECEMBER
4
O Christmas Tea: A British Comedy
When catastrophe strikes at James and Jamesy’s Christmas tea party, flooding the world with tea, the duo conjure wildly funny…
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DECEMBER
4
Oysters & Ales @ Bella Union
Oysters & Ales is back for our 28th season at Bella Union! Every Thursday from October through April, join us…
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DECEMBER
5
Andre Nickatina @ Grape Street Bar
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DECEMBER
5
Jeff Kloetzel @ DANCIN Vineyards
Great music, outstanding wine and stunning views!
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DECEMBER
5
Phil Reed @ South Stage Cellars
Catch Phil of the Brothers Reed singing solo at South Stage!
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DECEMBER
5
Rogue Party Bus Krampus Krawl
Join Rogue Party Bus in your finest Krampus or Krampus-Inspired costumes as we hit the town and travel to multiple…
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DECEMBER
5
Rogue Suspects: Bonnie Raitt @ Dos Mariposas
There’s nothing like a little Rogue Suspects & Bonnie Raitt to get you into the holiday spirit!! This show will…
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DECEMBER
5
Rogue Valley Royals Hockey Game
Come to the Rrrink to cheer on Medford's USPHL Hockey Team!
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DECEMBER
5
Sip & Shop @ Naumes Suncrest Winery
Join us for a festive evening of sipping, shopping, and celebrating local talent at Naumes Suncrest Winery! What to expect: -Browse a…
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DECEMBER
5
The Pozitronics @ RoxyAnn Winery
Back by popular demand, the Pozitronics’ Funky Disco Dance Party is coming back, at RoxyAnn Winery on Friday December 5th!
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DECEMBER
5
Upwind Groovers @ Dunbar Farms
Upwind Groovers is a group of white water rafters with instruments in hand. We’re a six piece band playing country/…
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DECEMBER
6
Central Point Community Christmas
Mark your calendars now for our Community Christmas event! Pine Street will come alive with festive floats, dazzling lights, and…
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DECEMBER
6
Fork in the Road @ Dunbar Farms
Fork in the Road is a dance oriented, classic-rock band playing classic rock and dance tunes from the 60s, 70s,…
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DECEMBER
6
Holiday Market @ CraterWorks
MAKERS MARKET – SAT. DECEMBER 6th, 10–2 🔥 Some folks shop. Others make. Come see what happens when our members turn…
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DECEMBER
6
Home for the Holidays
Join the Rogue Valley Choral Association for the third annual Home for the Holidays concert, featuring all four RVCA ensembles…
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DECEMBER
6
Jacksonville Holiday Parade
Our small town parade is big at heart. The historic setting, delightful procession of smiling faces and the celebration of…
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DECEMBER
6
Providence Festival of Trees
Join us for the 34th Annual Safeway | Providence Festival of Trees for Public Viewing at the Medford Armory! Tickets sold…
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DECEMBER
6
Rogue Winterfest Weekend Events
The 23rd Annual Rogue Winterfest's Weekend Holiday Event returns with fun for the entire family! The public is invited to…
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DECEMBER
6
Winter Lights Festival - Downtown Medford
Join us for some festive family fun as we celebrate the season! Activities include: - Tree lightning - Light parade - Appearances by Santa -…
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DECEMBER
7
Holiday Market @ Del Rio Vineyards
We invite you to get in the holiday spirit and join us for a sip and shop experience in our…
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DECEMBER
10
Drag Bingo & Buffet @ The Beatrice
We are excited to host Medford's favorite Lady Luci La Vicious for our monthly Bingo night. An evening of fabulous…
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DECEMBER
12
Bells & Balls Pickleball Tournament
Pickleball Heights is excited to present the 2nd annual Bells and Balls Pickleball Indoor Tournament on December 12th-14th. 🗓️ The tournament…
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DECEMBER
12
Jeff Kloetzel Holiday Vibes @ Dunbar Farms
Join us to hear Jeff play a selection of Christmas songs, as well as his usual repertoire of great music!…
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DECEMBER
12
Lisa & Dean @ DANCIN Vineyards
Great music, outstanding wine and stunning views!
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DECEMBER
12
The Nutcracker Ballet
Southern Oregon’s most cherished holiday tradition returns this December as Studio Roxander brings The Nutcracker back to the stage! Experience…
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DECEMBER
13
A Christmas Carol – the Musical
Step into the magic of the holiday season with this vibrant musical adaptation of Charles Dickens’ A Christmas Carol! This…
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Family, Outdoor Adventure, Things to Do, Trails
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The leaves are turning amber spice is in the air the beautiful valley is calling you to find adventure everywhere! Looking for the perfect place to sip a latte, or hike among the foliage? View our complete guide to enjoying fall in the Heart of the…  Read More
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Spring is a beautiful season to explore this charming city nestled in the heart of the Rogue Valley. With its mild climate, stunning natural surroundings, and vibrant community, Medford offers something for everyone. Whether you're seeking outdoor adventure, cultural experiences,…  Read More
Family, Outdoor Adventure, Things to Do, Trails
Whether you are training for your next major event or tuning up for the local Turkey Trot, Medford and the Rogue Valley are a runner’s paradise. With terrain to suit any runner’s needs, the region offers limitless options and is…  Read More
Attractions, Dining, National Park, Outdoor Activities, Outdoor Adventure, Things to Do, Wine
The leaves are turning amber spice is in the air the beautiful valley is calling you to find adventure everywhere! Looking for the perfect place to sip a latte, or hike among the foliage? View our complete guide to enjoying fall in the Heart of the…  Read More
Dining, Fishing, Guides & Tours, Jetboats, Lakes & Rivers, National Park, Outdoor Activities, Outdoor Adventure, Things to Do, Trails, Wine, Winery
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