Aspens, Adventure + Activities Abound! From Film Festivals to Oktoberfests to Trail Runs, Here's Everything Worth Marking on Your Fall Calendar
Summer's warm, easygoing days are winding down, but here in Grand County, that just means the best season of the year is about to begin. Every year around this time, I'm reminded all over again why fall in the mountains is my favorite; there's something about it that just feels like magic. Mornings arrive crisp and frosty, the high peaks start catching their first dusting of snow, and the aspens are just showing off with their vibrant gold, orange, and red everywhere you turn. The pace of life eases up too, leaving plenty of room to get outside in the cooler air and soak it all in. It's honestly one of my favorite times to hit the trails, cast a line, or squeeze in a few more rounds of golf before the season winds down. And even with school back in session, the weekend festivals and events keep right on coming. So I’ve put together some of the highlights to help you take advantage of this golden stretch before the lifts start turning again for winter!
SEPTEMBER 10-13: WINTER PARK FILM FESTIVAL
The Winter Park Film Festival got its start back in 2023, pioneered by two of our own: Connor Nelson and Parks Thomson, who both grew up right here in Grand County. They took what they learned out in the world and brought it home to share with our community, and now we get to experience world-class cinema in our little mountain town. They’ll have a huge variety of independent cinema. Think high-adrenaline action sports, narrative features, short films, and documentaries with a special focus on mental health, recovery, and disability.
This year the festival runs September 10–13, 2026, based again out of The Foundry Cinema & Bowl in Fraser. For four days, The Foundry turns into a hub of film screenings, meet-and-greets, and community events. Check out the full schedule and film guide to get a better idea of what the weekend will look like. A free Secret Screening at Deno's kicks things off on Thursday, September 10 from 3:30 to 5:00 PM. It’s “secret” because the film stays under wraps until showtime. And the best part? No need to plan ahead or RSVP: you can just show up!
You can buy tickets for individual showings or purchase passes for the weekend. A Full Festival Pass runs $150 and gets you into all three days of screenings, the awards ceremony, and the weekend's outdoor activities. For those who want to go all in (and directly support the festival's growth) there's also a $2,400 Red Carpet Pass, a sponsorship-level tier that includes priority seating, front-row spots at the awards ceremony, complimentary food and drinks around the festival, and an invite to the exclusive Peggy's Cinema Cabin opening-night party. Hop online and get your tickets and passes in advance!
And I love how the festival incorporates social opportunities and prioritizes getting people outside, not just in a theater all day! Each morning kicks off with a coffee meetup at Grand County Roastery, followed by your pick of adventure: a group hike led by an award-winning filmmaker and ultramarathon runner, fly fishing, or just a morning walk or run through the valley. On Friday evening, there's film trivia at Fraser Valley Distilling (8pm) followed by free late-night golf at Birdie Lounge (starting at 10pm), plus a live music festival night at Pepe Osaka's (home to my favorite fish tacos) on Saturday, September 12, where filmmakers and guests can gather to discuss the day’s big lineup of screenings. This year's keynote speaker is Josh Berman, the founder of Level 1 Productions (think twenty years of groundbreaking ski films and the streaming-on-Netflix documentary Full Circle). Josh is speaking Saturday, September 12 at 2pm.
And of course, things wrap up in true Winter Park style: a gondola ride up to Sunspot Mountain Lodge for the closing awards ceremony, with live music, mountain views, and plenty of celebration! For a town our size, it's pretty amazing to see something this big, built from the ground up by “local kids” who love this valley. It's one of those events that makes you proud to call Grand County home.
SEPTEMBER 12: UPSLOPE BACKCOUNTRY TAPROOM
Living the motto "Beer Tastes Better After an Adventure," the team at Upslope Brewing Company is planning its 11th Annual Backcountry Tap Room. It's just like it sounds: a beer hut at the end of a hike. Some say "earn your turns." This is more like earning your drinks!
This year, the Backcountry Tap Room has a new home: the top of Winter Park Resort’s new Wild Spur lift, sitting at 12,060 feet. Take the gondola up, then follow the marked Lower Roof of the Rockies Trail about 1.5 miles to the tap room (3 miles round trip). If you're feeling ambitious, take the optional Fantasy Meadows Loop for more mileage, totaling about 5.2 miles. (Regardless of your route, everyone takes the gondola back down.)
On tap this year, you'll find some tried-and-ture favorites like Upslope Craft Lager, Mary Jane Ale, Oktoberfest, and Blackberry Lemon Sour, alongside Snowmelt Hard Seltzer and Stem Ciders Off-Dry. And you can try their newest option: Fast + Light Series IPA, a hoppy 2.8% ABV brew.
Your ticket to the event ($44 + fees) gets you the gondola ride, the hike, and four drink tickets (good for one specialty pour and up to three more). Prefer to skip the beer? A non-drinker/kids-over-16 ticket ($20 + fees) covers the hike-only experience. Check-in starts at 8:45 am, with the gondola departing at 9:00 am on Saturday, September 12. You can even add on lunch when you purchase your ticket: pick from Roast Beef & Swiss, Basil Pesto Chicken, or a Vegan Wrap, all served with chips (gluten-free options available for a $4 add-on).
And I love that Upslope supports Leave No Trace with this event: 50% of event profits go directly to support Leave No Trace's work protecting the outdoors. So you can know you're giving back while enjoying a fall day in the mountains!
SEPTEMBER 12: HEADWATERS CENTER OKTOBERFEST
You can still get your tickets to the Headwaters Center Oktoberfest: Raising Steins for Streams, happening September 12th from 3:30–7:30pm at the Headwaters Center in Winter Park. The Headwaters Center is so much more than a coveted spot for weddings and events! It exists for a beautiful cause: raising awareness for water conservation in a county that boasts the headwaters of the Colorado River. Oktoberfest is a fun way to support that work, with proceeds from admission, the bar, and the silent auction all going toward the Headwaters River Journey Museum and other local water conservation education efforts.
Tickets range from $50 to $150 depending on how you want to celebrate: the $50 “Drop In for the Cause” gets you festival admission, a commemorative stein, two drink tickets, and a Bavarian pretzel; $80 “Festival & Feast” adds the full buffet; $110 “Stein & Dine” combines the buffet with a stein and two drinks; and the $150 “All In for the Cause VIP Experience” covers the buffet, a stein, unlimited drinks, and reserved seating.
SEPTEMBER 12: SNOW MOUNTAIN RANCH TRAIL RUNNING FESTIVAL
The YMCA of the Rockies' Snow Mountain Ranch is such a a gift to our community, hosting kids camps, cross-country ski clinics, and offering one-of-a-kind experiences for locals and visitors alike. The Snow Mountain Ranch Trail Running Festival returns this year on Saturday, September 12th, offering something for every level of runner. With options ranging from a fun 5K or 10K to the Half Marathon, 33K, or the challenging 50K, it's a great way to take in our fall's golden aspens and mountain views while enjoying well-marked trails and friendly aid stations. For those looking to go big, the Moosehead and Baby Moose Challenges let you tackle multiple races in a single day. Whether you're chasing a personal best or just soaking up the fall colors, it's a community event that celebrates running right in the heart of Grand County! Online registration has closed for this year, but race-day registration and bib pickup open at 5:30 AM for anyone hoping to jump in last minute. You can learn more here.
SEPTEMBER 12-13 WINTER PARK ART FESTIVAL
Head over to Cooper Creek Square in downtown Winter Park (also home to West and Main’s office!) for the Winter Park Art Festival. Stop by Saturday from 11am – 7pm or Sunday 11am – 6pm.
The Winter Park Art Festival brings two full days of art, music, and community fun. This annual juried show features an incredible lineup of local and national artists with original works in painting, sculpture, photography, ceramics, glass, wood, and more.
Best of all, it’s free to attend! Since Cooper Creek Square is zoned as an entertainment district, you can stroll with a drink in hand while browsing over 40 vendors, enjoying live music, and soaking up the lively mountain-town vibe. It’s a perfect weekend to connect with neighbors, support artists, and take advantage of a fall weekend in the mountains.
SEPTEMBER 14-20: GRAND LAKE'S CONSTITUTION WEEK
Grand Lake packs in an entire week worth of celebration every fall. The 15th Annual Constitution Week in Grand Lake runs all week long and brings the community together to celebrate American history and civic life. Events are free and open to the public, with weekday activities at the Grand Lake Center and fun youth-focused activities like go-karts, bumper cars, pedal boats, and miniature golf. Concerts, speakers, flyovers, and more make this an event the whole town is proud to put on! The event is capped off with fireworks over the lake on Saturday, September 20th. While you’re out there, grab a bite to eat at one of Grand Lake’s incredible dining options!
SEPTEMBER 17: GRAND KIDS LEARNING CENTER BERT + ERNIE GOLF TOURNAMENT
Back this year for its milestone 50th(!) Annual Golf Tournament, Grand Kids Learning Center celebrates fall with a “Fall Weekend” of fundraisers, kicking off with the Bert and Ernie Golf Tournament this year. A local favorite, the golf tournament brings a day of competition with teams of four and a shotgun start at world-class Pole Creek Golf Club, complete with panoramic mountain views and surrounding fall colors. They pull out all the stops with fun games and surprises out on the course, a welcome bag, an on-course lunch, and a post-party with appetizers, awards, and prizes at the clubhouse. This year they're upping the spirit game with a Best Costume prize for the most creative kid-inspired look and a Best Themed Team prize for the group that brings the most personality to the course. You can register your team of four here. Mark your calendars for Thursday, September 17 with a 10 AM shotgun start.
SEPTEMBER 18: GRAND COUNTY CASINO ROYALE
Bust out your best James Bond attire for this year's Casino Royale event. The Grand Foundation puts on this annual event to raise funds for the Opportunity for Youth Fund, which provides financial assistance to Grand County youth whose families lack the resources to cover the cost of activities their kids have earned the chance to participate in. The fund helps pay for student trips to places like Costa Rica, France, and Washington, D.C., covers brain bowl fees, athletic camps, sports clinics, and AP testing registration, and supports Grand County nonprofits and schools offering youth enrichment.
This year's event runs September 18th from 6:00–10:00pm at the Headwaters Event Center in Winter Park. Try your luck at craps, roulette, blackjack, or Texas Hold'em, all for a great cause. Individual tickets are $100 (with opportunities to sponsor tables, food, and more) and get you complimentary food and drinks, $200 in chips, and a full night of casino-style fun, all while supporting opportunities for Grand County youth. You can register here.
SEPTEMBER 18-19: ROCKY MOUNTAIN WINE FEST
Nothing pairs quite like a glass of great wine and those jaw-dropping mountain views you find at Winter Park Resort, and that's what Rocky Mountain Wine Fest brings every fall. Set against the backdrop of changing leaves and the Continental Divide, this two-day celebration brings unlimited samples from dozens of expertly selected wines and spirits from around the world, plus small plates, live music, and a whole lot of mountain charm. Once again, the event benefits the National Sports Center for the Disabled (NSCD).
Things get rolling Friday evening, September 18, with an opening evening event at The Lodge at Sunspot from 5-7pm, featuring small bites and premium wine pairings (note: this requires a separate ticket from Saturday's festivities). Saturday kicks off with a Riedel Wine Tasting Seminar at Hill House from 11am-12:30pm, where a professional sommelier walks you through how glass shape shapes flavor (and you get to take home a four-glass Riedel kit worth $112). Then the main event: the Grand Tasting in the Village at Winter Park, from 1-4pm, with unlimited pours, small plates, and live music from Jeremy Short and The Fretliners. Want to go big for the wine fest? The Rendezvous VIP Wine Pavilion adds exclusive access to hand-picked wines and a premium charcuterie station right by the Village Gazebo. And as a bonus, your event ticket gets you 50% off a scenic gondola ride through September 27th. Whether you're a serious wine aficionado or just here for the views and the vibes, grab your tickets online and get ready for a weekend of sipping and soaking in the fall colors.
SEPTEMBER 18-20: OKTOBERFEST
The 7th Annual Oktoberfest Hop Crawler is back this fall! Gather a crew, buy your tickets, and walk, ride, or take The Lift to Fraser and Winter Park's five breweries: Big Trout Brewing, Camber Brewing Company, Fraser River Beer Co., Hideaway Park Brewery, and Vicious Cycle Brewing. Grab your Hop Crawler ticket for just $35 (plus taxes and fees) and enjoy a free 10 oz pour at each participating brewery, plus an official medal and a souvenir pint glass to take home (the first 200 people to sign up). Each brewery will feature a special Oktoberfest-style beer, and while you have the whole weekend - September 18th through 20th - to make your rounds, Saturday, September 19th comes with extra fun like a stein relay, keg rodeo, stein holding contest, boot chug, and pretzel eating contest at each stop along the crawl. Pick up your medal and pint glass (required to participate) at the Winter Park Chamber of Commerce (right by the moose statue in downtown Winter Park) anytime that Thursday-Sunday from 9am-4pm.
SEPTEMBER 19: GRAND KIDS LEARNING CENTER FALL FESTIVAL
Rounding out the "Fall Weekend" that kicks off with the Bert and Ernie Golf Tournament on Thursday the 17th, Grand Kids Learning Center is hosting its 25th Annual Fall Festival on Saturday, September 19th at the Rendezvous Event Center in downtown Winter Park. Always a community favorite, the festival brings fun for the whole family, with games and activities for all ages - live music by Johnny O., harmonica lessons for kids, bounce houses, face painting, axe throwing, and soft-tip archery. And even better - it benefits our community! Adults can also enjoy local beer and whiskey tastings, and there will be a variety of food trucks. Swing by for an hour or stay for the afternoon. The event runs from 1-6pm. Entry is free, and tickets may be purchased for fun games and activities.
SEPTEMBER 26: ELEVATION EVEREST
If "earning your turns" is your love language, Elevation Everest made have you at hello. Hosted by Winter Park Resort, the endurance challenge is elevation gain to the max: participants hike or trail-run up the mountain and ride the gondola back down, repeating the loop again and again until they've hit their goal. Each lap climbs 1,600 feet over 2.2 miles, starting from a 9,100-foot base camp and topping out at a 10,700-foot turnaround point. Go solo or team up for a relay (2, 3, or 5 people) and choose your challenge: a Half Everest at 14,516 feet of total gain, or a Full Everest at 29,032 feet (matching the height of Mount Everest itself). Between laps, base camp gives a little reprieve from the grind, with DJs, saunas, cold plunges, yoga sessions, and food stations to keep you fueled and recovered. This year’s event is already sold out, but you can go to the base of the resort to cheer on the competitors and keep it on your radar for next fall if it sounds like the challenge you've been waiting for!
SEPTEMBER 26: NATIONAL PUBLIC LANDS DAY
Headwaters Trails Alliance is once again leading the charge for National Public Lands Day on Saturday, September 26. Grand County is proud to host the longest-running annual NPLD celebration in the nation, now in its 32nd year! There's a project for nearly every interest and skill level, from easy, family-friendly options to more strenuous work for those looking for a bigger challenge. Unless otherwise noted, projects run 9am-3pm, and while a full shift is appreciated, any amount of time you can give is always welcome!
This year's lineup of projects includes trail access and surface improvements on the BLM Skyline Loop near Kremmling, a river cleanup along the Colorado River at Pumphouse Recreation Area (which also requires signing up separately with Protect Our Rivers if you're bringing a watercraft), trail maintenance in Gore Canyon, a family-friendly river and creek cleanup between Fraser and Winter Park, native revegetation work in Fraser, trail blazing along the Continental Divide Trail in downtown Grand Lake, river restoration in Hot Sulphur Springs, winter trail prep on the Leland Creek loop, and turnpike repairs on Creekside Trail outside Fraser. If you're up for something more strenuous, Rocky Mountain National Park is building natural log foot bridges across Bowen Creek near Grand Lake, a hike-in project for volunteers 18 and older, which also requires a second sign-up at RMNP's registration page.
After a day of giving back, everyone (whether you volunteered or not) is invited to a free celebration in the park at the Rendezvous Event Center from 4:30-7:00pm on Saturday, with live music, a beer garden, informational booths, and giveaways. Register here to sign up for a project. And for those who want to extend the weekend, there's a bonus Sunday cleanup at the top of Berthoud Pass, open to all ages, followed by a BBQ.
OCTOBER 3: GRAND PARK RECREATION CENTER FALL OPEN HOUSE
If you haven’t had the chance to check out Grand Park Community Recreation Center, would just like to spend a morning at the rec, or are weighing a move to the area and want to see what our local indoor recreation hub looks like, the annual Fall Open House is the perfect opportunity. On Saturday, October 3rd from 9am-1pm, you can try out all the activities and just see what the facility has to offer. Activities include swimming, gymnastics, crafts, and climbing. Admission is free for GPCRC members and $10 for non-members.
We're lucky enough to have endless outdoor opportunities in Grand County, but there's something special about having a true community hub indoors, too (especially on those sub-zero winter days!). The Rec Center is a place for all ages and every kind of activity: whether you're in for a workout, your kids are at gymnastics practice, or the whole family is spending an afternoon at the pool, it's become a gathering spot that keeps the community connected and active year-round. The Fall Open House is a great opportunity to get active, explore the facility, and enjoy a fun fall morning with the community!
FALL-ING IN LOVE WITH GRAND COUNTY?
The fall color coupled with all the fall festivals and events makes it easy to see why people love this place, especially this time of year. Whether you're just looking for mountain getaway from the hustle and bustle of the city, ready to put down roots here, or see what an investment mountain real estate looks like, I'd love to share my decades of Grand County experience and real estate knowledge to help you find your dream property! Reach out to schedule a complimentary consultation. Hopefully, you'll just be around the corner from all the events and outdoor opportunities by next fall!
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