May in the Mountains: The Trails Are Yours
iTrip Aspen Snowmass · May 2026
Low snowpack means hiking and biking trails are open weeks early and the town is still blissfully yours to explore.
May is Aspen’s best-kept secret.
Locals call it “mud season,” but this year, there’s almost no mud. Thanks to an unusually low-snow winter, the hiking and biking trails that typically emerge in June are already dry, clear, and calling your name weeks ahead of schedule. Add in quiet streets, unhurried restaurant service, and boutiques actually willing to chat with you, and you have something rare in this famously busy mountain town: space to breathe.
If you’ve ever wanted to experience the best of Aspen and Snowmass without the traffic, the waitlists, or the shoulder-to-shoulder gondola crowds this is your window. Here’s how to spend it well.
HIT THE TRAIL
Hiking: Out Early & Uncrowded
This May, the lower and mid-elevation trails are already bone-dry. Get out before the summer crowds discover them.
EASY · IN TOWN
Start from the John Denver Sanctuary behind Aspen’s post office for a flat, paved-to-dirt ramble that follows the Roaring Fork River all the way to Glenwood Springs — a glorious 42 miles if you want to go long, or a breezy out-and-back stroll for something easy. Already dry and open. Dogs welcome on a leash. This is a great trail to train for your upcoming summer road race!
Flat · Dog Friendly · Paved + Dirt
MODERATE · PANORAMIC VIEWS
A local favorite right from town with steady switchbacks that lead to a panoramic overlook above downtown with Aspen Mountain as a backdrop. Roughly 3.8 miles roundtrip. You can extend it into Hunter Creek for a full half-day loop through meadows past historic abandoned cabins.
~3.8 mi RT · From Downtown · Accessible Early
EASY · ALPINE FEEL
A peaceful riverside ramble on gravel through riparian habitat just east of town, mostly flat and ideal for wildlife watching. With low water and no crowds in May, this is one of the best spots to catch a glimpse of deer or a red-tailed hawk, maybe even a moose, without another soul in sight.
Flat · Wildlife Viewing · Riverside
MODERATE · SNOWMASS VILLAGE
Crossing through the Two Creeks area of Snowmass, the Tom Blake Trail weaves through sublime aspen groves. Pair it with the Rim Trail for a rewarding climb to the best vantage point over Snowmass Village and the surrounding peaks. Tom Blake is the more moderate of the two, with the Rim Trail featuring some steep switchbacks but the view is so worth it!
Snowmass Village · Aspen Groves · Mountain Views
TRAIL TIPS FOR MAY
Maroon Bells access requires a shuttle or reservation starting mid-May — book ahead at www.visitmaroonbells.com
Higher alpine trails (Cathedral Lake, American Lake) may still have lingering snow. Please check trail conditions before heading out
Start early as afternoon storms can build quickly even in May
Layers are essential; mornings at 8,000 feet are still brisk
ON TWO WHEELS
Biking: A Gold-Level Destination, All to Yourself
The Roaring Fork Valley is an IMBA Gold-Level Ride Center and in May, you’ll share miles of trails with almost no one.
“There’s no better time to ride the Rio Grande Trail than May — dry, quiet, and the mountains are watching you the whole way down the valley.”
EASY · CLASSIC
Rio Grande Trail — Aspen to Woody Creek Tavern
The full 42-mile route from Aspen to Glenwood Springs loses elevation the entire way. You will enjoy this gentle, glorious downhill ride that follows the Roaring Fork River through some of Colorado’s most beautiful valley scenery. Ride it all the way down, then take the RFTA bus back up-valley to Aspen. Most spring and summer buses are equipped with bike racks, making the return trip easy and affordable. Or simply head out to Woody Creek Tavern (8 miles), stop for lunch on the patio, and loop back at your own pace. Perfect for e-bikes (Class 1 allowed from Emma Road to Aspen), families, and anyone who wants big scenery without a strenuous climb.
Downhill One-Way · RFTA Bus Return · E-Bike Friendly · Paved + Gravel
INTERMEDIATE · SCENIC
Castle Creek Road to Ashcroft Ghost Town
Depart from downtown and wind along Castle Creek Valley through elk-dotted meadows and dramatic Elk Mountain peaks to the historic ghost town of Ashcroft. A 24-mile roundtrip that earns its views. Bring a camera to photograph the old mine buildings against the spring sky as they are something special.
~24 mi RT · Historic Route · Intermediate
SINGLETRACK · LOCAL FAVORITE
Hunter Creek Valley & Smuggler Mountain Road
From the top of Smuggler Mountain Road, a network of singletrack trails branches into Hunter Creek Valley. Here you will find a system that Aspen locals ride year after year without tiring of it. The trail dips through groves of aspen, river crossings, and open hillside with views back toward town. This is for the more experienced mountain biker. For those looking for more moderate, flowy trails try out
From the top of Smuggler Mountain Road, a network of singletrack trails branches into Hunter Creek Valley. Here you will find a system that Aspen locals ride year after year without tiring of it. The trail dips through groves of aspen, river crossings, and open hillside with views back toward town. This is for the more experienced mountain biker. For those looking for more moderate, flowy trails try out Sky Mountain Park when it opens on May 16th.
Singletrack · Local Favorite · From Town
Need a bike? Silver City or Four Mountain Sports both offer excellent rentals including e-bikes, and can set you up with maps and local recommendations tailored to your ability.
DINING
Restaurants: World-Class Tables, No Wait
Many of Aspen’s best restaurants stay open through May and off-season means attentive service, special prix-fixe menus, and a genuinely relaxed atmosphere that hits different than the hustle and bustle of peak season.
SEAFOOD · OPEN YEAR-ROUND
517 E. Hyman Ave. An Aspen institution since 2018, Clark’s is the go-to for fresh oysters, caviar, lobster rolls, and chowder served at a marble raw bar in the beloved former Little Annie’s space. Open for lunch, happy hour, and dinner every day. Clark’s is one of the few restaurants in town running a full schedule in May. The lively atmosphere and exceptional seafood make it a perfect reward after a morning on the trails.
Open Daily · Lunch, Happy Hour & Dinner · Oysters & Seafood
SUSHI · ASPEN CLASSIC SINCE 1991
533 E. Hopkins Ave. One of Aspen’s most beloved restaurants, Kenichi has been serving world-class contemporary Japanese cuisine since 1991. The moody, candlelit room with warm cedar, lacquered wood, and the quiet theatre of the sushi bar is the perfect setting for a long, unhurried May dinner. Start with the signature Yellowtail Serrano, then let the evening unfold over nigiri, the Wagyu hot rock, and one of the deepest sake lists in Colorado. Open nightly, except for Sunday, for dinner.
Open Nightly Except for Sunday · Dinner · Sushi & Japanese
MEXICAN · LUNCH, HAPPY HOUR & DINNER
205 S. Mill St., upstairs. A colorful, festive second-floor dining room with mountain views, sizzling tableside fajitas, house-made tortillas, ceviches, and some of the best margaritas in Aspen. Las Montañas is open seven days a week for lunch, happy hour, and dinner. Just maybe, during off-season you may find they extend happy hour specials well into the evening. Pull up a patio seat and watch the quiet May streets below.
Open Daily · Lunch, Happy Hour & Dinner · Mountain Views
AMERICAN · HISTORIC COTTAGE
302 E. Hopkins Ave. Set inside one of Aspen’s oldest buildings, a Carpenter Gothic miner’s cottage built in 1883, the White House Tavern is the #1-rated restaurant on TripAdvisor Aspen and a consistent local favorite. The menu is focused and brilliant: premium sandwiches, hearty salads, and classic cocktails served in a warm, wood-paneled room with an exhibition kitchen. You will hear many a local comment on the chicken sandwich! Open daily for lunch and dinner. No reservations — walk-ins welcome, and in May you’ll actually get a table without a 2 hour wait.
Open Daily · Lunch & Dinner · No Reservations Needed
SHOP & EXPLORE
Shopping: 50+ Independent Boutiques, Zero Crowds
Aspen’s five walkable downtown blocks are home to more than 50 independently owned shops.
FASHION · LOCAL LEGEND
Open since 1969, the second-oldest retail store under continuous family ownership in Aspen. A curated mix of men’s and women’s fashion that has dressed this town for half a century and an essential stop for anyone who wants something that feels genuinely local.
Since 1969 · Men’s & Women’s
OUTDOOR GEAR & MORE
The go-to outfitter for backcountry touring, telemark, and cross-country gear is currently shifting into spring hiking and trail mode. The staff here have actually done the hikes they’re recommending. Pick up trail maps, layers, and any gear you need before heading out.
Outdoor Gear · Expert Staff
LOCAL ARTISAN CO-OP · VOTED #1 GIFT SHOP
315 E. Main St. Voted Aspen’s #1 gift shop four years running, the Emporium is an artisan co-op featuring over 100 local Colorado artists under one roof. It’s the opposite of a chain store. Inside you will find a rambling maze of rooms packed with handcrafted jewelry, paintings, pottery, sculptures, local food products, and one-of-a-kind treasures you won’t find anywhere else. The kind of shop where you walk in for five minutes and emerge an hour later with something you didn’t know you needed. Open daily.
100+ Local Artists · Handmade & One-of-a-Kind · Open Daily
WOMEN’S BOUTIQUE · LOCAL SINCE 1997
400 E. Hyman Ave. Owner Jill Murphy has been a fixture in Aspen since opening Misstyx in 1997 — nearly three decades of curating women’s apparel, jewelry, handbags, hair accessories, and gifts with a genuine local sensibility. The boutique balances Colorado-made jewelry and local designers with international pieces chosen for individuality over label. Small, approachable, and welcoming in a way that peak-season shopping rarely allows. In May, Jill is there, she knows her stock, and she has time for you.
Local Since 1997 · Women’s Apparel & Jewelry · Colorado Designers
ART & CULTURE
Aspen is quietly one of Colorado’s strongest art markets. The galleries along Mill Street and Hopkins Avenue carry work ranging from Western landscapes to contemporary sculpture — and the May quiet means you’ll actually get to speak with gallery owners about the work. A completely different experience from peak season browsing.
Art Galleries · Walkable District
THE BOTTOM LINE
Come in May. Beat Everyone Else.
The mountain trails are open and dry. The restaurants are world-class and actually have tables available. The shops have time for you. And the views…the Elk Mountains standing sharp and snow-capped against a deep blue May sky are the same ones everyone else will be paying peak-season prices to see in July.
Aspen rewards the traveler who shows up before the crowd. This May, the window is unusually wide. We suggest you use it.
Ready to Plan Your May Escape?
Browse our hand-picked Aspen and Snowmass vacation rentals many of which are perfectly positioned for easy access to trails, dining, and everything the valley has to offer this spring.
Browse Rentals at iTrip Aspen Snowmass
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