Fall for Winthrop: Autumn Events and Activities in Winthrop, WA

A crisp breeze sweeps through the North Cascade mountains and chases away the heat of summer. Gold and orange leaves dance on trees through Methow Valley. This beautiful scene can only mean one thing– Autumn has arrived in Winthrop, Washington.

In fall, this small mountain town comes alive with festivals, markets, outdoor adventures, and delicious seasonal treats. Here are some autumn activities we look forward to every year.

Winthrop Events

Every season brings a reason to celebrate in Winthrop, but autumn’s events take the cake.  Here are a few of the fall festivals that highlight the town’s heritage, culture, and lively spirit.

Labor Day Rodeo

When: August 31 - September 1



Held over Labor Day weekend, this classic rodeo brings cowfolk and fans together for barrel racing, roping, and bull riding. It’s a perfect way to experience Winthrop’s wild Western roots while enjoying one last big summer send-off.

Winthrop Vintage Wheels

When: September 13

If you’re more into horsepower than horses, this annual vintage car show may be more your speed. From restored classics to rare models, car enthusiasts and casual visitors alike will love strolling through downtown Winthrop as vintage automobiles line the streets.

Cidergrass Music Festival 
When: October 24 - October 26

Also known as the Winthrop Folk & Roots Festival, Cidergrass celebrates music from the Methow Valley and beyond. Expect toe-tapping rhythms, rich harmonies, and plenty of spiced cider to go around, all against the backdrop of brilliant autumn scenery.

Christmas at the End of the RoadWhen: November 27 - November 29

As the fall fades into winter, Winthrop likes to kick off the holiday season in style with “Christmas at the End of the Road”. A beloved holiday tradition, the town sparkles with festive lights, Santa makes an appearance, and fireworks brighten the night sky (the only time of year fireworks are allowed!). It’s the perfect way to say goodbye to autumn and hello to winter in small-town style.

Methow Trails Events

Not all autumn events happen in town. Winthrop is surrounded by the famous Methow Trails, a world-class trail system that winds through some of the most scenic terrain in the Northwest. 

Methow Trails are open all year long, but autumn is an especially gorgeous time to wander through the forest. Here are a few events hosted by Methow Trails at the beginning and end of the season.

Cutthroat Classic

When: September 6

This 11-mile trail run takes participants through the rugged beauty of the North Cascades. With alpine lakes, golden larches, and sweeping mountain views, the race is as much about the scenery as the challenge.

Methow Trails Film Fest

When: December 4

Though just outside the autumn season, this event celebrates the Methow Valley through film. You are encouraged to create a short film to share your story, or simply come to enjoy the show!  It’s an intimate way to connect with the spirit of the region after spending time outdoors.

Autumn Eats

If you aren’t a fan of festivals and fairs, you can still enjoy the harvest season. Food is at the heart of autumn, and as the temperatures dip, Winthrop’s food and drink scene offers the perfect places to savor local flavors.

Methow Valley Ciderhouse

A must-visit during apple season, the Methow Valley Ciderhouse celebrates the region’s orchards with handcrafted hard ciders made from locally grown fruit. The laid-back taproom is perfect for enjoying a drink and a delicious meal, made with top-quality ingredients and served by friendly staff. With hearty meals and an outdoor patio overlooking the mountains, it’s a quintessential fall stop.

Old Schoolhouse Brewery

Set along the Chewuch River, Old Schoolhouse Brewery has long been a favorite for both locals and visitors. The brewery is known for its award-winning beers, from hoppy IPAs to smooth porters, and the lively pub atmosphere makes it a great place to unwind after a day on the trails. Seasonal beers often make an appearance in the fall, giving guests a chance to sip something unique while enjoying live music or river views.

Lost River Winery

For wine lovers, Lost River Winery is a gem tucked right into Winthrop. The winery specializes in small-batch, handcrafted wines that showcase Washington’s diverse vineyards. Their tasting room offers a relaxed and intimate atmosphere to sample bold reds, crisp whites, and elegant blends. It’s the perfect spot to spend a slow afternoon and bring home a bottle (or two) for the holidays.

Fainting Goat Restaurant

If you’re looking for a memorable dinner, the Fainting Goat Restaurant delivers with a menu built around seasonal produce, sustainable meats, and fresh seafood. The restaurant blends rustic, western charm with a touch of sophistication, offering dishes that are both hearty and refined. From autumn-inspired pastas to perfectly seared steaks, it’s the kind of place where a leisurely meal turns into the highlight of your evening.

Enjoy Autumn at Freestone Inn and Cabins

If you are looking for the perfect place to enjoy fall in Winthrop, stay with us at Freestone Inn and Cabins. 

Located in Mazama, just a few miles from Winthrop, Freestone Inn offers a variety of accommodations to fit your fall vibes. For a cozy, mountain lodge experience, enjoy a beautiful suite in the main lodge. If you’re looking for a more immersive autumn adventure, our dog-friendly, early winter cabins keep you close to the trails. 

Freestone Inn is surrounded by all the things that make autumn in the North Cascades so beautiful. Book Now!