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LOCAL
COMMUNITY
EVENTS
January
The Sasquatch Outpost ·
Rabbit Hole Adventures with Jim Myers of the Sasquatch Outpost is now booking for the upcoming 2026 season! If you’ve been thinking about stepping deeper into Colorado’s wilderness, now’s the time. Rabbit Hole Adventures offers guided experiences designed
for different comfort levels — all rooted in time spent off the grid, intentional exploration, and the possibility of Sasquatch activity.
Introductory Night Hikes
A 4–5 hour guided night hike near Bailey, ideal for those curious
about Sasquatch research but not ready for an overnight expedition.
Multi-Day Camping Expeditions
Fully supported, all-inclusive backcountry trips that immerse you in remote wilderness
for several nights — offering extended time in areas where activity is more likely.
Horseback Camping Expeditions
A unique blend of wilderness camping and backcountry horseback travel, adding an entirely different dynamic to the experience as horses remain alert to nighttime activity around camp.
Dates for the upcoming season are now available.
Learn more and purchase tickets at rabbitholeadventures.co
Choose your adventure — and follow where the trail leads.
Jan.9th,10th,11th,16th,17th,18th,23rd,24th,25th,30th,31st
Snowshoe & Fondue
Join us for Aspen Peak Cellars original Snowshoe & Fondue event,
a classic Colorado day of fun (10:30AM -3:30PM)
including, snowshoes & poles, guided snowshoeing, appetizers, wine tasting, authentic Swiss cheese fondue, glass of wine, live music, guides and winery staff gratuity, sales tax.
Check-in for the event is 10:30-11AM at the winery, off-site snowshoeing or
winter hike from 11-1:30PM, tasting, fondue & live music from 1:30-3:30PM
back at the winery.Event is for adults, 21+ only, must present valid ID
during check-in. Provide your own transportation from winery to trailhead
and back, ride share is not a reliable source of transportation in the
Bailey area.Sorry, pets are not allowed on the trails or at the winery/bistro.
All Snowshoe & Fondue Tickets must be purchased for a specific date, not
flexible, are non-refundable, but transferable to someone else.
Rain, shine or Snow! Over the past 15 years, we rarely had to cancel an
event because of weather, unless Hwy 285 is closed due to adverse road
conditions. Snow days are lot of fun and after all, it is a snowshoe event.
Aspen Peak Cellars
60750 US Highway 285, Bailey, CO. (303)-816-5504
Call ahead for more details & register
January 2, 2026 @ 5:00 pm - 8:00 pm Fairplay: Kevin Russo & Chris Gissenger Live Music
Fairplay: Kevin Russo & Chris Gissenger Live Music
Highside Brewing-Fairplay 411 US Hwy 285, Fairplay, CO, United States
Live Music with South Park locals Kevin Russo & Chris Gissenger every Friday evening from 5-8p @ Highside Fairplay
Aspen Peak Cellars
60750 US Hyw 285, Bailey, CO.
Bingo!
Thursday, January 15th & Feb. 19th, 7:00 – 9:00pm
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Potluck at 6pm, Bingo at 7pm.
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Fairplay Library
Is your New Year's Resolution to craft more? To meet new faces? To focus on finishing your work in progress sitting in a corner? If you answered yes to any of these questions or you just need a space to create, then come join us at the Fairplay Library for our Wednesday night Craft n' Chats! Create together from 4pm-6pm every Wednesday. See you there!
400 Front St, Fairplay, CO 80440
Phone: (719) 836-4297
Calling all local families!
HIPPY is SNOW excited to invite you to a FREE Family Snowshoe Day. Bring the kids, bring your friends, and get ready for some winter fun!
No snow? No problem! We’ll turn it into a family-friendly hike instead . Afterward, warm up with hot cocoa and story time -the coziest way to wrap up the day.
All are welcome
Snowshoes are provided
Fun is guaranteed
Please share with friends and neighbors—we’d love to see everyone there!
