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By | 11/15/2021 | Featured Articles, Outdoor Adventure, Things to Do

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!

SEPTEMBER
23
A Midsummer Night's Dream @ OSF
When Hermia, Lysander, Helena, and Demetrius flee into the woods, they do it in pursuit of personal freedom and their…
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SEPTEMBER
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Chicago @ Britt
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SEPTEMBER
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Emma @ OSF
Jane Austen’s beloved Regency-era heroine takes center stage in this fast, funny, feminist adaptation by Kate Hamill, featuring contemporary pop…
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Jacksaphine Count(r)y Fair
Join us for a week of events celebrating the beauty, flavors, and diversity of the Applegate Valley shared by Jackson…
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Pozitronics @ Local Vines Wine Bar
This week is shaping up to be unforgettable at Local Vines Wine Bar! We’re excited to bring you two fantastic…
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SEPTEMBER
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Smote This, A Comedy About God @ OSF
Back by popular demand, this sharp and hilarious solo show follows actor Rodney Gardiner as he attempts to abandon God—no…
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SEPTEMBER
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Two of a Kind @ Tap & Vine
Wednesday, September 23rd • 5-7pm ☀️ On the patio (weather permitting 😂 IYKYK) John Dickerson & Bridget Best are bringing classic rock…
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SEPTEMBER
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Yellow Face @ OSF
When DHH—a Chinese American playwright and staunch activist—protests the casting of a white actor in Miss Saigon, he never imagines…
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SEPTEMBER
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Ashland Folk Collective: Mama's Broke
Mama's Broke is the Canadian folk duo of Amy Lou Keeler and Lisa Maria, known for blending traditional folk from…
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August Wilson's King Hedley II @ OSF
It’s 1985, and King returns to his family and community, determined to take control of his life after having served…
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Come From Away @ OSF
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Rogue Valley Growers & Crafters Market
Experience the best of local flavors at Rogue Valley Growers & Crafters Market! 🌿 Join us in Ashland every Tuesday…
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Sip & Succulent @ Long Walk Vineyard
Join us at Longwalk for a super special evening. Who doesn’t love wine and succulent gardens?! Thursday, September 24th at 6pm.…
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The Taming of the Shrew @ OSF
Sweet-natured Bianca has her choice of suitors, but there’s a problem: she can’t get married until her older sister, Kate,…
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SEPTEMBER
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Traditional Irish Music @ Dunbar Farms
Join us for our first live music performance of the year! A company of talented musicians jam with traditional Irish…
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SEPTEMBER
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Xtreme Bar Bingo @ Rocky Tonk Saloon
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SEPTEMBER
25
Henry IV, Part One @ OSF
King Henry IV is in trouble: a faction of his allies, including a valiant youngster named Hotspur, have turned on…
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SEPTEMBER
25
Justa Duo @ Trium Wines
Fuuunn Frieeyyey!! 🕺Sure thing!!! 💃🏻Sept 25th@5pm!! 🎶Justa Duo 🎵 beautiful patio vibes, fantastic wines, ciders, beers, seltzers, bubbles, Latin Fusion…
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SEPTEMBER
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Senior Community Day at Medford's Railroad Park
The Medford Railroad Park welcomes local retirement communities and senior citizens to the park on Friday, September 25, from 11…
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SEPTEMBER
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The Brisbane Project @ RoxyAnn Winery
Join us at RoxyAnn Winery for a Friday night of dancing and fun as we welcome Southern Oregon’s Brisbane Project…
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SEPTEMBER
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Empire Lockers Storage Unit Garage Sale
Storage Facility Tenant & Community Garage Sale! Storage unit tenants & community members will have their units open to sell…
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SEPTEMBER
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Fall Plant Sale
Coming soon! OSU Master Gardener native plant sale is right around the corner. See you there! (Just so happens to…
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Harvest Festival @ Pheasant Fields Farm
Come experience everything fall at the farm has to offer! Ride The Great Pumpkin Express, pick out the perfect pumpkin,…
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SEPTEMBER
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Made in Southern Oregon - Fall Edition
September is right around the corner and that means our fall Made in Southern Oregon event is coming soon! Registration…
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SEPTEMBER
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Medford Multicultural Fair
A free, one-day celebration of culture at Medford’s Pear Blossom Park. Entertainment, games, and food highlight the event.
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SEPTEMBER
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Nick Garrett-Powell @ StoneRiver Vineyards
Saturday at StoneRiver is shaping up to be a good one. NICK GARRETT-POWELL takes the stage from 5–7 PM for an…
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SEPTEMBER
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Ride the Rogue
Join us on Saturday, September 26, 2026, for a spectacular day of cycling through the beautiful Rogue River Valley. Whether…
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SEPTEMBER
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The 2026 KS Wild Annual Dinner
We invite you to celebrate our shared public lands for KS Wild and Rogue Riverkeeper's biggest fundraiser and party of…
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SEPTEMBER
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The Brothers Reed @ Dunbar Farms
The Brothers Reed, Saturday September 26th, 6-8pm The Brothers Reed are back at Dunbar Farms! Folk/Bluegrass/Americana with edgy sibling banter, The…
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SEPTEMBER
26
The Roadsters @ Walkabout Brewing
Walkabout Brewing Company and The Oregon Booking Agency present: The Roadsters 6:00-8:00 pm - Lawn Genre: Rock / Country / Pop / Dance The…
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SEPTEMBER
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Adam Gabriel @ Del Rio Vineyards
Acoustic soul, southern-born, west coast seasoned, singer-songwriter, Based in Southern Oregon. Blaze n Monkey food truck will be on site.
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SEPTEMBER
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Bryan Oliver @ Tap & Vine
Wrap up your weekend with live music from Bryan Oliver, a Southern Oregon favorite known for his wide‑ranging style and…
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SEPTEMBER
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Jeff Kloetzel @ RoxyAnn Winery
Jeff has been the local opening act at the renowned Britt Festival for artists such as America, Chicago, Natalie Merchant,…
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SEPTEMBER
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Medford Railroad Park Sunday Run Day
The park, at Table Rock Road and Berrydale Avenue in Medford, will be open from 11 a.m. to 3 p.m.…
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SEPTEMBER
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Petty Thievery @ Dos Mariposas Vineyard
Tom Petty tribute band
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SEPTEMBER
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Sunday Summer Market
This Sunday at the Troon Sunny Summer Market — all summer Sundays from Noon to 4 p.m. An amazing group…
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SEPTEMBER
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The Rosa Lees @ Wooldridge Creek Vineyard
Join up-and-coming bluegrass band, The Rosa Lees, for a high energy set of music at Art in the Vineyard at…
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SEPTEMBER
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The Scottish Fish @ Dos Mariposas Vineyards
The Scottish Fish are making their way back along the West Coast and we are one of their favorite stops…
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SEPTEMBER
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Jeff Kloetzel @ Tap & Vine
Join us for a spring evening on the patio with live music from Jeff Kloetzel; a seasoned singer‑songwriter known for…
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Jim Gaffigan @ Britt
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OCTOBER
1
End of Summer Music : The Brothers Reed
Free Community Concert - The Brothers Reed Oct 1st 5-6:30pm Circadian Cellars- Wine available to purchase - ON and OFF…
OCTOBER
2
Chamber Music Concerts presents Fry Street Quartet with Toby Appel, Viola and Monica Ohuchi, Piano
The Fry Street Quartet is a trailblazing ensemble known for its “blend of technical precision and scorching spontaneity” (The Strad).…
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OCTOBER
2
Homestead Charm Vintage Faire
Join us October 2nd and 3rd for an unforgettable vintage event at the heart of the rogue valley at Hanley…
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OCTOBER
2
October First Friday Art Walk!
First Friday Art Walk: October 2, 2026 5:00 p.m. - 8:00 p.m. Join us for First Friday Art Walk! We are thrilled to…
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OCTOBER
3
Daniel Nickles Band @ Pheasant Fields Farm
Join the Daniel Nickels Band at Pheasant Fields Farm for a special Harvest Festival Makers Market featuring over 50 vendors,…
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OCTOBER
3
First Annual Sip & Stroll for Polio
Help eradicate polio one tasting at a time during Medford Rogue Rotary Club’s First Annual “Sip & Stroll for Polio”…
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OCTOBER
3
Happy Tails Festival
🐶 4TH ANNUAL HAPPY TAILS FESTIVAL 2026! 🐾 Join us for a Free! fun-filled day celebrating dogs, pets, families, local businesses,…
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OCTOBER
3
OKTOBERFEST
What can you expect? 🍖 Delicious Food: Savor traditional Oktoberfest treats and more! 🎶 Live Music: Enjoy festive tunes to get you…
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OCTOBER
3
Oktoberfest
Tap & Vine at 559 is hosting Oktoberfest at The Village Medford Center. Join us for German Food, Beer & Bands This…
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OCTOBER
3
Rogue Valley Lions Wine Walk
The 4th Annual Harvest Wine Walk is just around the corner, join the Rogue Valley Lions for a special evening…
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OCTOBER
3
Rogue Valley VeteRUN 5k 2026
559 followers • 30 following The Rogue Valley VeteRUN is a 5K Fun Run & Fundraiser. We support local and national…
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OCTOBER
3
Sip & Stroll for Polio
“Sip & Stroll for Polio” is a creative way for people to enjoy a variety of drink tastings in downtown…
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OCTOBER
3
Talent Harvest Festival
You ready for a rocking good time? Robbie Dacosta and his band will help us celebrate Halloween! Activities include: -Free live…
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OCTOBER
3
Talent Harvest Festival Fun Run
Let’s kick off Fall with The Best Race of the Year!
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OCTOBER
3
The Apology Tour @ The Holly Theatre
The Resolve Apology Tour is a live storytelling event created by Resolve Center that brings anonymous apologies to the stage…
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Featured Articles, Outdoor Adventure, Things to Do
Winter break is the perfect time to explore the Rogue Valley and enjoy all that Southern Oregon has to offer. Whether you’re looking for outdoor adventures, cozy indoor activities, or great local food and wine, Medford is the ideal home…  Read More
Dining, Featured Articles, Outdoor Adventure, Things to Do, Wine
In Medford, the most meaningful keepsakes can’t be packed in a suitcase — they live in the laughter of a crisp hike, the warmth of a shared meal, and the glow of a Rogue Valley sunset.This winter, skip the souvenirs…  Read More
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Winter steelhead fishing on the Rogue River in Oregon is an exhilarating experience that draws anglers from across the nation. Nestled in the scenic Pacific Northwest, the Rogue River offers some of the best winter steelhead fishing opportunities. This comprehensive…  Read More
Featured Articles, Outdoor Adventure, Things to Do
Winter break is the perfect time to explore the Rogue Valley and enjoy all that Southern Oregon has to offer. Whether you’re looking for outdoor adventures, cozy indoor activities, or great local food and wine, Medford is the ideal home…  Read More
Dining, Featured Articles, Outdoor Adventure, Things to Do, Wine
In Medford, the most meaningful keepsakes can’t be packed in a suitcase — they live in the laughter of a crisp hike, the warmth of a shared meal, and the glow of a Rogue Valley sunset.This winter, skip the souvenirs…  Read More
Featured Articles, Outdoor Adventure
Winter steelhead fishing on the Rogue River in Oregon is an exhilarating experience that draws anglers from across the nation. Nestled in the scenic Pacific Northwest, the Rogue River offers some of the best winter steelhead fishing opportunities. This comprehensive…  Read More
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