Labor Day seems to be everyone’s perfect excuse for one last hurrah before summer comes to a close and the kiddos head back to school.

Before we begin to mourn the fading summer and turn our attention to fall and all things pumpkin spice, we’re here to help you plan that final summer fling, with fun for the whole family throughout Central Oregon.

Hayden Homes Amphitheater’s stage glows beneath a low-hanging sun, with stage fog, colorful lights and a full audience.

Hayden Homes Amphitheater – Photo by Gwen Shoemaker

Hayden Homes Amphitheater – Oregon’s Largest Outdoor Music Venue

This Labor Day weekend, right along the Deschutes River in Bend’s Old Mill District, Hayden Homes Amphitheater is gearing up to help you get your holiday weekend started early by welcoming Dominic Fike to the stage Thursday, Sept. 3, for a night that blends alternative pop and indie rock with notes of hip-hop and R&B. You may also recognize him from the HBO Original Series “Euphoria,” as Fike has more recently pursued a career in acting alongside his musical career. His newest album, “Rocket,” was released in summer 2025 and will feature songs from the album alongside other works during his “Comedy Tragedy Parody” tour.

Then, on Sunday, Aug. 6, “Weird Al” Yankovic takes the stage with more comedy and parody, though in a much different way than Dominic Fike’s performance, keeping us all on our toes with his “BIGGER & WEIRDER” 2026 Tour. Think comedy meets rock, with parodies of some of the biggest musical stars, including Madonna, Michael Jackson and Taylor Swift. Many of his hits include personalized parodies like “Smells Like Nirvana” and “Like a Surgeon,” or arguably his most recognized, “White & Nerdy.” With special guest Puddles Pity Party, it’s a performance that will have you dancing and laughing, with the best of both worlds of a concert and comedy show.

A large group of people in colorful inner tubes float down the Deschutes River, with some waving at the camera and Hayden Homes Amphitheater in the background.

Deschutes River Floaters – Photo by ALIVE Co.

Deschutes River Float

Before the summer heat dies down, how does one final river float sound? The Deschutes River remains a hot commodity in September, when the weather is still beautifully warm for a refreshing dip in the river. If you’re a local, maybe you already have your own tube and know exactly what the drill is. For those visiting from out of town, though, hauling your own tubes along for the trip isn’t exactly convenient. That’s where Tumalo Creek Kayak & Canoe comes in, with all the river-floating rental gear you need to hit the water. More information can be found in our Go With the Flow and Float Like a Pro blog, where we cover all the bases, from rental gear and shuttle passes to local tips and tricks for getting the most out of your Deschutes River float!

The Old Mill District’s 25th Anniversary Celebrations

Here in the Old Mill District, we’re inviting the community to celebrate our 25th Silver Jubilee with a mix of activities, in-store specials and dining experiences throughout the District. Here’s a sneak peek at some of the fun planned for you this Labor Day weekend.

Free Spirit Yoga + Ninja + Play: Just in time for Labor Day weekend and running throughout the month of September, Free Spirit is offering $25 off 10-class passes for Adult Yoga, Toddler Open Play and Kids Open Play with the inclusive discount code FREESPIRIT25OFFSALE. It’s a totally fun way to let your kiddos get those back-to-school jitters out and a good way for you to find some relaxing movement too!

A table display at BUDD + FINN features souvenirs including candles, coasters, mugs, books, maps and posters.

BUDD + FINN – Photo by Gwen Shoemaker

BUDD + FINN: Swing by BUDD + FINN this Labor Day weekend to snag yourself a limited-edition “25th Anniversary” 8 oz candle with notes of balsam fir, vetiver and pine. Each candle is poured into a sturdy amber glass jar in collaboration with Landmark Fine Goods in Sisters, Oregon. The candle is arriving just in time for cozy fall vibes and makes a great way to bring a little bit of the Old Mill District Celebration home with you. Even better: Over Labor Day weekend only, BUDD + FINN will offer guests who spend $100 or more a choice of a free limited-edition anniversary candle or 25% off their entire purchase, a nod to 25 years well spent.

Lubbesmeyer Art Studio & Gallery: This Labor Day weekend just so happens to line up with First Friday Art Walk, and the Lubbesmeyer’s 25th Anniversary special offering. On Friday, Sept. 4, stop by to say hello to artists Lisa and Lori and find out how every guest can win a prize, ranging from original art pieces to generous discounts.

Warby Parker: Shop for new eyewear at Warby Parker and enjoy in-store giveaways throughout the holiday weekend, running Friday through Sunday, Sept. 5-7.

Tumalo Creek Kayak & Canoe: Enjoy the Labor Day Scratch and Dent sale offering discounted gear and demo equipment running Sept. 5-13. The theme? You guessed it! The Old Mill District’s 25th Silver Jubilee Anniversary!

Old Mill District Dining and Patio Celebrations

The Old Mill District offers plenty of inclusive dining options, with scenic patios along the Deschutes River that make it easy to turn a day of shopping into a relaxing afternoon or evening by the water while enjoying more 25th Anniversary celebrations and specials. Here’s what to look for this Labor Day weekend.

Overhead view of a pasta dishe and a salad from Pastini, served with a basket of bread and a glass of wine.

Pastini – Photo by Gwen Shoemaker

Pastini: For the occasion, Pastini is offering a special Deschutes Spritz as a limited-time cocktail that draws inspiration from Bend’s river views and high desert landscape through a tempting blend of Crater Lake Vodka, prosecco, elderflower liqueur finished with a lemon and raspberry simple syrup offered all month long.

Va Piano Vineyards Wine & Champagne Bar: Raise a glass and cheers to the 25th Anniversary with 25% off all bottles and glasses of its 2022 DuBrul Cabernet Sauvignon starting just in time for your Labor Day weekend and running through the rest of the month!

Ben & Jerry’s: What is a celebration without a sweet treat? Ben & Jerry’s is offering a specialty sundae, “Bill’s Mill Chill,” as an ode to the founder of the Old Mill District and Hayden Homes Amphitheater, Bill Smith, with a blend of some of his favorite ice cream flavors. If you’ve spent much time in the District or at the Amphitheater, it kind of goes without saying that Bill had great taste, so his favorite ice cream flavors are sure to be the perfect fit for the occasion.

For more great dining around the District, check out our Golden Hour Dining blog and our Inclusive Cuisines blog for more culinary finds to enjoy during your Labor Day weekend!

Central Oregon Beauty!

Is it even a true Bend weekend done right if you don’t get out and enjoy some good old-fashioned nature and hiking trails? In a world of advanced technology, take advantage of one of the final weekends before back-to-school by unplugging, getting outside and hitting the trails.

Early morning view of Smith Rock with the river flowing at its base, surrounded by trees before sunrise.

Smith Rock – Photo by Hardebeck Media

Kick things off with Smith Rock State Park, a quick 26-mile drive from Bend, you’ll find about 12 trails to choose from, offering something enjoyable for every hiking level. Start with an easy trail like the 0.5-mile Rim Rock Trail, with beautiful views of the park, or try the steeper 1.5-mile Canyon Trail, which connects you to the river system and reveals the signature boulder that resembles Woodstock from the classic Snoopy comic strip. Feeling up for a challenge? Set off on Smith Rock’s most well-known trail, Misery Ridge. Don’t let the name intimidate you because once you hit the top of the 3,360-foot summit, the view makes it all worth it.

Next on the list is the highly popular Steelhead Falls Trailhead, located in Terrebonne about 25 miles north of Bend. The trail offers a 0.5-mile hike to the nearby waterfall and is known for its beginner-friendly trail, beautiful picnic scenery, fishing hotspots and campsites.

We know hiking can take up some time, and weekends can be tough when you’re trying to squeeze everything in. For a similar beginner-friendly hike with stunning waterfall views only about 14 miles from Bend, Tumalo Falls is a great place to take hikers of all abilities. With the famous waterfall just 700 feet from the main parking lot, Tumalo Falls provides breathtaking views without the commitment of a long hike.

More Around Town

Bend Comedy Festival will be hooting and hollering this Labor Day weekend. Join in on the stand-up fun for the second annual nonprofit festival, celebrating all things funny, creative and community-focused, running Friday through Sunday, Sept. 4-6. This year’s lineup includes favorite acts like Geoffrey Asmus, Fahim Anwar, Cristina Mariani, ASSSSCAT and a slew of the best up-and-coming comedians from across the country. Purchase single-show tickets or festival passes, and don’t forget about the afterparties for passholders, including specialty cocktail discounts at San Simón and karaoke with comedians and comedy fans at the Dogwood at the Pine Shed.

A large raptor soars low over an audience of children and adults at the High Desert Museum during a Raptors of the Desert Sky show.

Raptors of the Desert Sky show at the High Desert Museum

For a great daytime activity for the whole family, check out the High Desert Museum, where guests can learn all about the High Desert region through indigenous wildlife, culture, art and history. This Labor Day weekend, the Museum will have special feature exhibits to browse, including Under Pressure: A Volcanic Exploration and Miguel Almeida: Las Manos que dan de Comer, alongside several permanent displays featuring fan favorites like Autzen the Otter and Raptors of the Desert Sky.

For a little cowboy flair, the Deschutes County Fairgrounds and Expo Center is hosting its ninth annual Cascades Futurity and Aged Event, where spectators can enjoy free admission to watch elite equestrian riders work with their horses to separate a single cow from the herd using instinct and precision. Additional activities include working-dog trial exhibitions and Western-inspired lifestyle vendors making it a yee-haw kind of weekend!

There you have it! A sneak peek at what’s in store for Bend locals and visitors this Labor Day weekend, with a little something for everyone to enjoy. Stay kind, be safe, and cheers to your final summer hurrah!