Test your lumberjack skills, enjoy a drag brunch, and more this weekend in the Vail Valley
Another busy weekend is on tap with flannel, food and fun
FreeFall Bluegrass Festival
This weekend marks the inaugural FreeFall Bluegrass Festival in Vail Village. This new event will run Saturday and Sunday and includes some fan favorites on the musical roster. The event fills a gap in the calendar that the town of Vail was trying to fill and offers free, family entertainment.
“Bluegrass is happy, family-friendly music with a large fan base. The town of Vail was looking for proposals to attract and entertain people during the shoulder seasons and October has been very busy since COVID hit and doesn’t seem to be slowing down,” said Diane Moudy of Resort Entertainment Group, a Vail-based full-service entertainment and event company with a 20-plus-year history of planning and servicing events throughout the U.S. and Mexico. “The intention is to brand and create a signature event that will carry on into the future.”
The lineup includes the who’s who of musicians on the bluegrass scene today. In fact, to close out the weekend on Sunday, the Bluegrass Generals features members of Leftover Salmon and the Infamous Stringdusters and more who come together to form this supergroup.
The talent for this show came together quickly all because of the relationships Moudy and the Vail Valley have built with the artists.
“With this being the inaugural year and budgets being tight, I went through my phone and called upon some of my famous bluegrass friends that the Vail Valley heavily supported throughout COVID and kept them working during that tough time, so they jumped at the opportunity to give back,” Moudy said. There are also local bands who will play as well.

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The concerts will be held at the Solaris Stage in Vail Village and the activities and music will go from 11 a.m. to 7:30 p.m. each day. Bring the family early to check out the Rock and Roll Playhouse. From 11 to noon, The Rock and Roll Playhouse band invites its core audience of families with children aged 1-7 to listen to songs created by the most iconic musicians in rock history. On Saturday, the music of the Beatles will be performed and on Sunday the music of the Grateful Dead will be performed. During the set change on the kid’s stage, Nick Steingart will play Saturday and Eleanor Hibbard, a 12-year-old singer/songwriter from Grand Junction will sing a few songs with Ryan Dart Duo on Sunday. The kids zone will also feature bounce houses as well as other kids activities throughout the day.
Once again, this whole weekend is free, so enjoy the last of the fall colors and bring out the entire family to enjoy FreeFall Bluegrass Festival. The event will be held rain or shine and outside food is allowed in the venue but not outside drinks, those will be available for purchase. For more information, a full schedule and FAQs go to .
Man of the Cliff

While FreeFall Bluegrass Festival is brand new, Man of the Cliff has been around for 13 years. The event celebrates fall, flannel, beards, and throwing things like axes and kegs. What’s your favorite “lumberjacktivity?” Man of the Cliff has a variety of competitions including ax throwing, keg tossing, caber tossing, speed chopping, archery and more. Who knows, you may earn the title of “Man of the Cliff” or “Woman of the Cliff” by the end of the day.
The beloved event takes place at Nottingham Park in Avon and starts at 9 a.m. this Saturday. Register for $88 in advance as space is limited for the competitions. Spectating is free but a $10 donation is suggested. Once again, Man of the Cliff has teamed with Can Do MS, an Eagle ¾Ã¾ÃÈȾ«Æ·ÊÓÆµapp-based nonprofit that provides programs and resources to help those living with multiple sclerosis and their families thrive.
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Beer goes well with flannel and all the activities at Man of the Cliff and this year the official beer partner is Peculier Ales, which is based out of the Windsor and Fort Collins communities on the Front Range. Come try the Old Mill light lager, Peach a la Mode Pastry sour or Hula Pie coffee milk stout. They will also serve peach mango Pool-Aid hard seltzers and The Sun Is Shining pale ale, Hopportunity Knocks hazy IPA and Baltic Way porter.
The kids are welcome to come to Man of the Cliff and can have some fun of their own at the Kid’s Zone with games and a bounce castle.
Get the party started early by heading to the Westin Riverfront Resort and Spa on Friday night at 6 p.m. Stop by the Stoke & Rye Terrace and grab your credentials and a drink and listen to live music by local band Gregger and the Balance. This party is not just for those participating in the event, it is open to the public. For more information, go to .
Mission Mt. Mangart

You may not realize it, but many of the ski areas around us and the outdoor industry as we know it today can be attributed to the members of the 10th Mountain Division. The 10th Mountain Division was the winter warfare unit that trained for battles in Europe during World War II just south of Vail at Camp Hale. Learn more about their story this Friday at Vail Mountain School during a screening of “Mission Mt. Mangart.”
The award-winning documentary was created by local extreme athlete and Warren Miller film star Chris Anthony. Anthony has been taking the film around the nation and overseas and it has received rave reviews.
These troops fought the pivotal battles of Mount Belvedere and Riva Ridge, for which the longest ski run on Vail Mountain was named. The 10th “did the impossible” and surprised Nazi Germany and broke down the Gothic Line in the Apennine Mountains in Italy.
“Mission Mt. Mangart” chronicles the events leading up to June 3, 1945, when a ski race was held in the former Yugoslavia, hosted and organized by the soldiers of the 10th Mountain Division.
The documentary has unique interviews with members of the 10th and footage from that era as well as reenactments of the race on Mt. Mangart, since no photos or footage could be found.
These film screenings are only done in person, so take advantage of seeing it this week at Vail Mountain School in East Vail. Doors open at 6:30 p.m. and the movie begins at 7 p.m. Tickets are $20. Proceeds from the evening will benefit the Colorado Snowsports Museum and the . For more information or to reserve your spot, please visit to learn more and to get tickets.
Lobster and Seafood Boil

Say goodbye to summer and enjoy Leonora restaurant at The Sebastian in Vail one more time before it closes for dinner service for the off-season.
“Every summer season we host a Summer Dinner Series with a rotating BBQ and seafood boil. These were very popular this summer and in high demand from our guests and owners,” said Jordan Harris, marketing manager with The Sebastian Vail. “We wanted to celebrate the end of the season for Leonora by throwing one last Lobster and Seafood Boil not only for our owners and guests, but for the community of the Vail Valley.”
In addition to the lobster and seafood, expect to find all the delicious sides. Executive chef Kevin Erving and his team will supplement the seafood with red potatoes, corn, paella, a warm sweet and savory potato salad and other creative salads. Save room for dessert. Preserved Palisade peach trifle, warm apple crumble and ginger molasses whoopies await those who saved room for the sweets.
The price is $175 per person and you can add wine pairings for $75. Guests can make reservations for this event on Saturday night at .
Halloween Drag Brunch

We are halfway through the month of October and Halloween happenings are starting to take place. Come out to Vintage in Vail Village for the Halloween Drag Brunch on Sunday.
Don your costumes for this annual event and maybe you’ll take home top honors in the costume contest. Support your local LGBTQ+ community and nonprofit Mountain Pride by making a reservation and sit back and have some fun. There is a $25 per person donation added to each bill for each reservation and that will benefit Mountain Pride.
There will be three drag shows hosted throughout the day. The first one will be at 10 a.m., the second at noon and the third will be a 2 p.m. Online reservations can be made at or call 970-479-0175. Be sure to select the dining experience and be seated indoors to see the show.
