As you begin making plans for your Telluride Labor Day weekend adventure, you probably already have a few ideas as to what you want to do. From a fabulous festival to amazing outdoor fun, there are many reasons our mountain town is so popular.
Why Labor Day Is One of the Best Late‑Summer Weekends to Visit Telluride
After a long and sweaty summer in your hometown, we can promise that a late summer visit to Telluride will feel like paradise. We aren’t known for getting too hot, and on a Telluride Labor Day weekend, the weather is bound to be absolutely perfect. Encouraging travelers and residents to get outside and play, to breathe deep of that crisp mountain air, and to relax as hard as they play, every minute will be filled with fun.
Families especially love our town during the holiday, and as you might expect, they love our family-friendly rentals in Telluride. Everyone is welcome in Telluride, and this list of things to do in Telluride Labor Day weekend is all the proof you need.
Outdoor Activities to Experience Over Labor Day Weekend
As we mentioned above, the beautiful weather over this holiday weekend will make you want to get outside and play. The activities listed below are some of our favorite things to do in Telluride for Labor Day weekend, and we know they will soon be yours as well.

Take a Hike
Every trail will be open and accessible this idyllic weekend in August/September, even the ones high on the mountain that may close in the next few weeks. This includes the Jud Weibe Memorial Trail, a 3+ mile-long loop that ascends over 1200 feet. Offering panoramic views of the town and the mountains, you can start your hike on Aspen Street in town.
- Length: 3.5 miles
- Difficulty: Moderate (Summer/Fall), Hard (Winter)
- Elevation Gain: 1,233 feet
- Trail Map
Stand Up Paddleboarding
There are two lakes in the immediate area, Trout Lake or Alta Lake, and on a beautiful late summer day, there is nothing more fun than paddling around either. The mountains reflect in still waters, and the first peek at fall leaves may be experienced with each dip of the paddle. Telluride Outside offers guided SUP tours if you are unsure about going out on your own.
Soaking in the Hot Tub
Luxury amenities are standard in our holiday havens, including hot tubs that may be bubbling merrily on the deck of your escape. Multi-taskers can include napping, sipping beer, and watching college football in their list of favorite things to do in Telluride for Labor Day.
Festivals, Live Music, and Local Events
Your Telluride Labor Day weekend fun is just going to keep getting better and better with festivals, live music, and other local events taking center stage.
Telluride Film Festival
Did you know that the Telluride Film Festival has been in existence longer than Sundance? And although 53 years of celebrating movies in all forms over Labor Day weekend doesn’t compare to the Cannes Film Festival (80 years), we have developed a more than respectable following. As a matter of fact, this wonderful film festival, offering workshops, meet-and-greets, and presenting 50+ films, is one of our town’s top draws for the holiday weekend.
Music on the Green
Our summer concert series, Music on the Green, is held at Reflection Plaza in Mountain Village on Fridays through October. Costing nothing to attend and offering a wonderful way to end a summer day on the mountain, bring a chair or a blanket to spread out on the grass and prepare for a night of family fun.
Telluride Farmers Market
Your Accommodations in Telluride retreat offer a fully equipped kitchen that is fun to stock with fresh produce, sweet treats, and other items from the Telluride Farmers Market. Held on Fridays from late May through early October, the event also offers guests a chance to shop for souvenirs, gifts, and art during their wanderings.

Restaurant Options for Relaxed Meals and Special Nights Out
All the time you spend exploring the things to do in Telluride Labor Day weekend will make you hungry, and we have some wonderful ideas to help you fill your belly.
Smuggler Union Restaurant & Brewery
Billed as the friendliest bar in Telluride, Smuggler Union Restaurant & Brewery offers a rustic cabin-like experience, an elevated pub grub menu, and an extensive beer, wine, and cocktail menu. Their Colorado Lamb Burger will never let you down, especially when accompanied by a Bat & Ball. No, we haven’t switched to baseball talk; a Bat & Ball is a Whistle Pig Rye Shot + 10 ounces of pilsner, and this drink is a winner in our books!
- Address: 225 S Pine St, Telluride, CO 81435
- Hours: 11:30 AM to 9 PM
- Menu
The New Tunnel Supper Club
There is no shortage of fine restaurants in Telluride, but The New Tunnel Supper Club offers a twist to your standard date-night dinner. This prohibition-era speakeasy offers a 6-course tasting menu hidden inside Clark’s Market and accessed through a secret kitchen entrance. There is only one seating, held nightly at 7:30 PM, and reservations are required, but it is definitely worth the extra effort. Their chocolate malt cake will make you wish you had eaten dessert first, and their martinis will make you feel like an extra in the Great Gatsby movie.
- Address: 700 W Colorado Ave #242, Telluride, CO 81435
- Reserve Your Table
Book Your Telluride Vacation Rental for Labor Day Weekend Today
A Telluride Labor Day weekend getaway is one that will linger in your heart for years to come. Reserve one of our Labor Day rentals in Telluride today and celebrate the end of summer with mountains and luxury!