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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
21
Complimentary Wine Tasting
Join us for complimentary wine tastings every Thursday and Friday from 4-6pm. Learn about different varietals and discover your favorites.…
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NOVEMBER
21
Naumes Suncrest Winery Varietals
Located in a timeless farmhouse that has been in the Naumes family for generations, the Naumes Suncrest Winery features a…
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NOVEMBER
21
Oregon Cabaret presents Pine Mountain Lodge
Featuring the classic standards of the 30s and 40s, Pine Mountain Lodge tells the story of a returning World War…
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NOVEMBER
21
Reading Between the Wines @ Sams Creek Cellars
Join us for a glass of wine and an uninterrupted hour of reading, followed by a social hour or more…
NOVEMBER
21
Rogue Valley Growers and Crafters Market
When you want the absolute best in Rogue Valley grown fresh produce, artisan foods and handcrafted gifts for your family,…
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NOVEMBER
21
Sip and Paint Pottery with Rogue Stonewear
Join us at one of our favorite Rogue Valley wineries for Sip and Paint Pottery with Benjamin! I'll bring a variety…
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NOVEMBER
21
The Sound of Music
The Sound of Music! Immerse yourself in the heartwarming story of Maria, a spirited young woman who brings joy and…
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NOVEMBER
21
Wine Tasting at DANCIN Vineyards
Taste beautiful wine at DANCIN's beautiful winery and tasting room. Set magnificently on the forested foothills of Southern Oregon overlooking…
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NOVEMBER
22
Free Music + Wine Series at Roxy Ann Winery
Visit RoxyAnn Winery for free live music from various artists alongside award-winning wine. Fridays: 6-8 pm Sundays: 4-6 pm
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NOVEMBER
22
Rogue Valley Royals vs Bremerton Sockeyes
Come on down to the Rrrink for some great hockey, cold beer and good friends!
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NOVEMBER
22
SOU Theatre presents: Museum
Museum takes place on the final day of a group show of three fictional contemporary American artists being exhibited in…
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NOVEMBER
23
Adam Gabriel & Emily Turner @ South Stage Cellars
This is going to be an amazing night! There are only 45 tickets available, so act fast!
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NOVEMBER
23
Applegate Uncorked Barrel Tour
Come celebrate growing season with a self-guided tour of the Applegate Valley Wine Country. Spring is the perfect time to…
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NOVEMBER
23
Drawing Animals @ Rogue Gallery & Art Center
Drawing Animals with Robert Arieas Ages 11 – 15 Saturday November 23, 1 – 4pm The class will look at the basic anatomy…
NOVEMBER
23
Drawing Animals with Robert Arieas
Ages 11 – 15 Saturday November 23, 1 – 4pm The class will look at the basic anatomy of a few animals…
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NOVEMBER
23
Free Family Day
Join us and explore processes of book-making, collage, and word play, all inspired by the collaborative visual and text works…
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NOVEMBER
23
Gingerbread Jubilee
Bring the whole family down to the Craterian Theater to see all of the fantastical gingerbread creations on display during…
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NOVEMBER
23
Holiday Bazaar @ Crater Rock Museum
Come join us for our annual Roxy Ann Gem & Mineral Society Holiday Bazaar at Crater Rock Museum. Admission to…
NOVEMBER
23
Native American Heritage Celebration @ Children's Museum of So. OR
Celebration of Native American Heritage Month ​​​ The Children's Museum is teaming up with the Office of Native Nations Liaison, Southern Oregon…
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NOVEMBER
23
Outlaw Cyclocross Race #5
Back to Tom Pearce for the final race of the series! Awards and fundraiser raffle. Category 4/5 (beginner, intermediate), clydesdale, singlespeed…
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NOVEMBER
23
Roxy Ann Gem & Mineral Society Holiday Bazaar
Come join us for our annual Roxy Ann Gem & Mineral Society Holiday Bazaar at Crater Rock Museum. Admission to…
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NOVEMBER
23
So. Oregon Runners Turkey Trot Run
Come to Talent, Oregon for our Thanksgiving run! We will be hosting a food drive for the SOU food bank…
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NOVEMBER
23
Whiskey Tasting @ Gold Rush Brewing
Tickets are now available for our Whiskey tasting event! Limited seats available so don’t wait November 23, 6-8pm Gold Rush Brewing 1100…
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NOVEMBER
24
Benefit Concert - Simple Dreams @ Belle Fiore Winery
Join Us for an Evening of Music and Giving! Simple Dreams, Southern Oregon's premier Linda Ronstadt tribute band, is hosting a…
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NOVEMBER
24
Friendsgiving Dinner and Games
SUNDAY 11/24/24 5pm-9pm Celebrate Friendsgiving with us at The Wine Lounge, where we we’ll be serving up delicious chili and…
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NOVEMBER
24
Sip and Paint Pottery with Rogue Stonewear
Join us at one of our favorite Rogue Valley wineries for Sip and Paint Pottery with Benjamin! I'll bring a variety…
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NOVEMBER
25
Oberon's Open Mic Night
Oberon's Open Mic taken to a whole new level! Music, beat poetry, stories, and occasional puppet show. Sign up is…
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NOVEMBER
27
Open Mic at the Phoenix Clubhouse
Every Wednesday 7-10pm, all ages and talents are welcome to join in on the fun at open mic night! Drums,…
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NOVEMBER
28
Southern Oregon Turkey Trot
Come to Talent, Oregon for our Thanksgiving run! We will be hosting a food drive for the SOU food bank…
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NOVEMBER
29
Festival of Light Celebration - Santa's Parade and Downtown Illumination
Join us for Santa's Parade and the Grand Illumination on Friday, November 29th in downtown Ashland!
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NOVEMBER
29
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
29
Jeff Kloetzel & Friends @ Dos Mariposas
You’ve probably heard the incredible Jeff Kloetzel around the valley, but this Black Friday, get ready for a special treat!…
NOVEMBER
29
The Festival of Light Celebration - Santa's Parade and Downtown Illumination
Join us for Santa's Parade and the Grand Illumination on Friday, November 29th in downtown Ashland!
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NOVEMBER
30
Christmas Celebration at 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
30
Poinsettia Festival and Holiday Bazaar
Saturday, November 30th, 2024 10:00am-4:00pm Join us inside the warm greenhouses for our Annual Poinsettia Festival. Walk through thousands of colorful poinsettias.…
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NOVEMBER
30
So. Oregon Artisan Market @ Rellik Winery
Join us for our fall inspired Southern Oregon Artisan Market at Rellik Winery! There will be amazing local artists to…
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NOVEMBER
30
Victorian Christmas
Each year, the unique town of Jacksonville transforms into an even more charming version of itself with twinkling lights, festive…
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NOVEMBER
30
Wreath Making at SOHS Hanley Farm
Once you’ve finished your “Black Friday” shopping, head over to SOHS Hanley Farm on Saturday, November 30. From 11am to…
DECEMBER
1
Aaron Reed @ Naumes Suncrest Winery
Aaron Reed live!! 2-4pm
DECEMBER
1
Floral Wreath Making Workshop @ Grizzly Peak Winery
oin a floral designer for festive crafting time together with the local flower harvest. You’ll be guided to make your…
DECEMBER
1
Holiday Music with Jeff Kloetzel @ Hummingbird Estate
Join us for holiday music with Jeff Kloetzel around the warm fireplace at Hummingbird. Enjoy a glass of wine and…
DECEMBER
1
Open Mic Night
Join us for Open Mic Night at the Wine Lounge in Jacksonville, OR every first and third Sunday of the…
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DECEMBER
1
Ornament & Mug Painting @ Paschal Winery
Paint a handmade mug and ornament made by local artist, Courtney from Burrow & Bloom Pottery, while enjoying award winning…
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DECEMBER
1
Sip and Paint Pottery with Rogue Stoneware
Join us at one of our favorite Rogue Valley wineries for Sip and Paint Pottery with Benjamin! I'll bring a variety…
VISIT WEBSITE
DECEMBER
1
Winter Market at the Village
Are you looking for unique gifts, fresh local goods, or just a delightful winter outing? And guess what? Santa will be…
DECEMBER
4
Chamber Music Concerts presents: Israeli Chamber Project
Join the Chamber Music Concerts Series for their 41st season and the fourth concert of the series featuring Israeli Chamber…
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DECEMBER
5
SOU Choirs present:
The SOU Chamber and Concert choirs present their fall concert titled: "The United States v. We the People" directed by…
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CLICK HERE TO SEE ALL EVENTS
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