Photo: stellamc/Shutterstock

America's 20 Coolest Outdoor Towns

United States Travel Outdoor
by Matador Creators Mar 23, 2016

THIS LIST COULD EASILY HAVE 100 PLACES. The US simply has so many canyons and rivers and slopes, so much coastline, all of it with rad little towns along the way.

So putting together this list, we narrowed it down with a few criteria:

  1. The place should be an actual town, not just a spot or destination. In other words, you can live/work there year round, and even in the “off-season” it’s still cool.
  2. The outdoor objectives that make the place so rad must be part of the immediate surroundings. If you can’t climb / ski / paddle / surf right in town, the access should be just beyond, not an hour away.
  3. The place should have a notable culture, tradition, or local economy around the activities (and natural resources) themselves. Of special mention are places such as Salida, where actual infrastructure has been developed (manmade whitewater features) that brings cool events and awareness to the town.

For obvious reasons, we came back with a high concentration of places out West (and in Hawaii/Alaska). May not be fair, but if you visit you’ll understand.

All this said, finding big lines can happen anywhere. Where I grew up in the southern Piedmont (forested, gentle rolling hills kind of terrain), a trickling neighborhood ditch became a gnarly class V kayak run if you caught it right after a thunderstorm.

The ultimate limitation is never the place but your imagination. Let us know the what kinds of lines you’re finding right in your town.

–David Miller, Senior Editor
Asheville, North Carolina

1. Haleiwa, HI

Photo: Ppictures/Shutterstock

Perfect day

Morning surf at the break of choice followed by coffee and pastries from Coffee Gallery in Haleiwa, or a fresh acai bowl from Haleiwa Bowls. If waves are blown out, hike or bike ride along the North Shore bike path to work up another big appetite, then spicy tuna quinoa salad from Pupukea Grill and laze around Waimea Bay til the sun goes down.

Honor roll

Beers: The pool bar or Surfer, the Bar at Turtle Bay — live music and drinks while you watch the sun go down over the ocean!
Eats: Haleiwa Bowls, Pupukea Grill, Waialua Bakery, The Elephant Truck, Lei Lei’s Bar & Grill, Coffee Gallery
Coffee: Coffee Gallery
Gear: Number 808, Guava Shop, Surf N Sea, Two Crows Surfboards
Music venue: Surfer, the Bar

2. Bishop, CA

Photo: Geartooth Productions/Shutterstock

Perfect day

Option 1 — Morning yoga, tea or coffee and breakfast at The Black Sheep, route climbing in the Owens River Gorge or Pine Creek. Soaking in hot springs. Home-cooked dinner with locally sourced beef and veggies. Option 2 — Morning road bike ride through Round Valley to Mammoth or out on HWY 6 toward Nevada. Bouldering session at the Buttermilks or Tablelands. Hot springs soaking. Dinner at The Mountain Rambler Brewery

Honor roll

Beers: Mountain Rambler Brewery (hand downs), The Black Sheep (happy hour 4-6 daily)
Eats: The Bishop Burger Barn, Thai Thai (at the Bishop airport). Mountain Rambler Brewery, Schats Roadhouse, Las Palmas
Coffee: The Black Sheep (the BEST)
Gear: Gear Exchange (consignment and new gear), Eastside Sports

Special thanks: Katie Lambert.

3. Chattanooga, TN

Photo: Sean Pavone/Shutterstock

Perfect day

Kayaking and whitewater rafting as well as SUPping are all prime and can be done in the city proper as well as nearby areas. There is also endless epic mountain biking as well a road biking. The bouldering at Little Rock City is on Signal mountain and offers some of the best sandstone climbing in the nation. The Tennessee Wall for both sport and trad climbing is epic. There are also over a dozen other local and in-town climbing spots. For those rainy and too hot days there are three indoor climbing gyms. Canyoneering is also really popular.

Honor roll

Beers: The Terminal Brewhouse
Eats: Aretha Frankensteins — punk rock breakfast for every meal, Sofa King Juicy Burger — grass-fed beef burgers, homemade ice cream, good beer, The Terminal Brewhouse — tavern food and drinks, Main Street Farmers Market on Wednesdays
Coffee: Milk and Honey — eco-farmed coffee
Gear: Rock Creek for new gear, The Gear Closet for used and consignment
Music venue: Mountain Opry goes off Friday nights

4. Salida, CO

Photo: aaronj9/Shutterstock

Perfect day

Winter — Monarch Pass for a day of ripping groomers at the resort or fresh turns in the backcountry. Best scenario is a non-holiday weekday after a storm, when it’s all untracked powder and nonexistent lift lines. Then head back into town for beers, burgers, and bluegrass at Benson’s. Summer — Hop on your mountain bike and haul up S Mountain with endless access to single track. Afternoon on the water, paddling. Plenty of put-ins on the Arkansas River upstream, in town, and downstream from Salida. Commercial operations run the Browns Canyon section north of town.

Honor roll

Beers: Benson’s, Elevation Brewing, Wood’s High Mountain Distillery (for current or aspiring whiskey lovers)
Eats: Amica’s — housemade pizzas and microbrews (limited seating so go early), Ploughboy for all-natural groceries, The Fritz, Laughing Ladies
Coffee: Cafe Dawn on G Street — tons of natural light and doesn’t mind if you post up for a while
Gear: Salida Mountain Sports right downtown, Subculture Cyclery
Music venue: The SteamPlant Theater, right on the river at the terminus of the local bike trail

5. San Luis Obispo, CA

Photo: HannaTor/Shutterstock

Perfect day

Surf check or predawn hike up Prefumo Canyon, then drive the See Canyon side (golden and beautiful in the early morning light) then down into Avila Beach for breakfast at KravaBowl (acai bowl). Shell Beach Ridge Trail or Bishop’s Peak afterwards, then beach time and a brew at Bang the Drum.

Honor roll

Beers: Bang the Drum Brewery
Eats: Foremost Wine Co., KravaBowl
Coffee: Scout Coffee
Gear: The Mountain Air
Music venue: SLO Brewing Company

6. Jackson Hole, WY

Photo: CSNafzger/Shutterstock

Perfect day

Option 1 — Morning mountain bike laps on Teton Pass, lunch at Elevated Grounds Coffee House, hike up to Phelps Lake in Grand Teton National Park and session the jump-rock on the north side of the lake, sushi and drinks at Sudachi to close out the day. Option 2 — Morning hike to Delta Lake in Grand Teton National Park followed by lunch at Dornan’s taking in the view of the Tetons, river surf session down at Lunch Counter Rapid on the Snake River, back to town for dinner at Local followed by a nightcap at the Rose. In winter, ski JMHR — Corbet’s if it’s in.

Honor roll

Beers: Snake River Brewery, Melvin Brewing, The Deck at the top of the Bridger Gondola
Eats: Teton Thai, Snake River Grill, Persephone, Pica’s
Coffee: Elevated Grounds
Gear: Skinny Skis , Teton Mountaineering
Music venue: The Pink Garter, The Million Dollar Cowboy Bar — best people watching in town and live country

7. Valdez, AK

Photo: Yongyut Kumsri/Shutterstock

Perfect day

Spend winter days backcountry skiing on Thompson Pass — via helicopter, snowmachine, or your own two feet. Ice climb the many waterfalls of Keystone Canyon. Hit up the groomed Mineral Creek cross-country trails. In summer, paddling takes precedence — run Lowe River and Mineral Creek, sea kayak Shoup Glacier. Halibut fishing, sport climbing and bouldering, trekking Valdez Glacier, and fly fishing for dollies on Robe River are also good options on gloriously long summer days.

Honor roll

Beers: Wheelhouse Lounge
Eats: Totem Restaurant for hearty breakfasts. Fish n’ chips Alaska-style at the Halibut House. Crab and steaks at T.H.C. Off the Hook Grill.
Coffee: Drive-thru espresso at Sacred Grounds or organic drip from Rogue’s Garden
Gear: Prospector Outfitters for everything from ABS packs to kayaks to guns and ammo
Music venue: The Pipeline Club

8. Moab, UT

Photo: Anthony Heflin/Shutterstock

Perfect day

Option 1 — Morning coffee and breakfast burrito at “Wake and Bake,” hike into Hunter Canyon for a little-visited backcountry arch (on your right). Grab a pint and burger for lunch at the Moab Brewery. Go to Arches National Park and make the 1.5-mile hike into Delicate Arch for sunset. Bring a headlamp and stick around to see the Milky Way rise behind the arch. Option 2 — Early morning coffee at Eklecticafe. Mountain bike vaunted red-rock trails, Slickrock and Amasa Back. Grab food-truck tastiness at Quesadilla Mobilla before heading out for a sunset tour in a Hummer through Moab Adventure Center.

Honor roll

Beers: Moab Brewery, Eddie McStiff’s
Eats: Cowboy Grill, The Desert Bistro, Quesadilla Mobilla, Zax Restaurant, Moab Diner
Coffee: Wake and Bake, Eklecticafe, Moab Coffee Roasters, Wicked Brew
Gear: Moab Adventure Center, Pagan Mountaineering, GearHeads
Music: Woody’s Tavern

9. Truckee, CA

Photo: Khanh Le/Shutterstock

Perfect day

Anything multi-sport springtime: Ski corn, downhill or cross-country mountain bike up Western States or Martis Peak and then wrap up the day with a fly-fishing session on the Little Truckee as the dry flies start popping. Maybe even a surf strike mission to SF if you can squeeze it in. Get a quick climb in up on Donner Summit at Snowshed or Blackwall…just to round it out.

Honor roll

Beers: A cooler by the river or at the Chamoix if you can make it before the sun goes behind tram face
Coffee: Coffee Bar on Jibboom or Wildflour in Squaw
Eats: Tacos Jalisco, or next door at Treat Box for a burger
Gear: The Backcountry, Tahoe Sports Hub, Start Haus does a great tune
Music venue: Moody’s

Special thanks: Tucker Patton.

10. Leavenworth, WA

Photo: Checubus/Shutterstock

Perfect day

Wake up early for a coffee and a hearty breakfast with a view. In summer, drive up Hwy 2 for a morning adrenaline rush at the downhill mountain bike park at Stevens Pass. Then paddle class-III Wenatchee or III/IV Skykomish. After that, get back into town (aka, “Der Town”) for beers and lunch at Icicle Brewery. Next best bet is to grab your rod and reel and head to the Wenatchee for the evening hatch or squeeze in some climbing on Washington’s best granite crags.

Honor roll

Beers: Icicle Brewing Company
Eats: Good Mood Food
Coffee: Argonaut
Gear: Leavenworth Mountain Sports
Music venue: Fest Halle

11. Lander, WY

Perfect day

Wake with the sun, throw your rack in the truck, and head into Sinks Canyon for epic trad and sport climbing. Sandstone, granite, dolomite, ice — if you can climb it, Lander has it. After climbing, continue up the canyon until it opens into a lush alpine meadow for picnic lunch — this is your taste of the remote Wind River backcountry. Don’t forget your fly rod to hook a few brookies. Cool off at Popo Agie Falls on the Middle Fork Trail. Should be beer-thirty by then.

Honor roll

Beers: Lander Brewing Company
Eats: The Middle Fork killer breakfast and lunch, Gannett Grill — grass-fed burgers on the patio
Coffee: Old Town Coffee
Gear: Wild Iris Mountain Sports
Music venue: Lander Bar

12. Fruita, CO

Photo: GROGL/Shutterstock

Perfect day

The “Moab of Colorado” is a two-wheel, red-rock dreamscape. Morning session biking the steep and technical Kokopelli area trails — Rustler’s Loop is a good warmup. Beat the afternoon heat rafting the Colorado River with a mellow, three-hour float down the Blue Heron Run. The sunset: a cavalcade of high-desert reds, yellows, browns, and oranges.

Honor roll

Beers: Copper Club Brewing Company for 18 Road IPA
Eats: Simple, fresh ingredients at Hot Tomato Pizza
Coffee: Aspen Street Coffee
Gear: Over the Edge for all your fat tire needs
Music venue: Community-supported Cavalcade hosts concerts, open mics, variety shows, etc

Special thanks: Veronica Daehn Harvey

13. Grand Marais, MN

Photo: Nquinn/Shutterstock

Perfect day

Summer outdoor recreation revolves around freshwater lakes — from massive Lake Superior to the Boundary Waters Canoe Area Wilderness — so bring your paddle. Over 100 miles of cross-country ski trails are enough to fill many winter days, but downhill skiers can also hit up nearby Lutsen Mountain, one of the midwest’s most-legit ski hills.

Honor roll

Beers: Voyageur Brewing Company
Eats: Crooked Spoon, My Sister’s Place, Gun Flint Tavern
Coffee: Java Moose
Gear: Stone Harbor
Music venue: Gun Flint Tavern

Special thanks: Eric Frost

14. Bend, OR

Photo: Kris Wiktor/Shutterstock

Perfect day

Perfect days in Bend begin with trad climbing at Smith Rock, where hundreds of routes ascend the riverside cliff face. Then SUP Deschutes River or tackle some of the almost 300 miles of single-track mountain biking. Stroll downtown for a bevy of brewpub options.

Honor roll

Beers: Deschutes Brewery lives up to its reputation, plus Bend’s roughly 12(!) other microbreweries and ale houses
Eats: Pilot Butte Drive-in for burgers, McKay Cottage Restaurant for breakfast and lunch
Coffee: Backporch Coffee Roasters serves up a mean espresso
Gear: Mountain Supply, Pine Mountain Sports
Music venue: Tower Theatre, Silver Moon Brewery

15. Montauk, NY

Perfect day

Blizzard precipitation and yet somehow strong offshore winds and barreling, 6 foot conditions. Post surf thaw at Coffee Tauk and then back to someone’s house to look at the video your friends shot of y’all out there getting snowy coverups.

Honor roll

Beers: Montauk Brewing Company, The Surf Lodge, Liar’s Saloon
Eats: Naturally Good Foods & Cafe, Joni’s Kitchen, Inlet Seafood — for the view alone, Montauk Bake Shoppe
Coffee: Coffee Tauk
Gear: Paddle Diva, Air & Speed Surf Shop
Music venue: The Surf Lodge, The Gig Shack

16. Hawi, Big Island, HI

Photo: Maridav/Shutterstock

Perfect day

Predawn drive on Kohala Mtn. Road through the small town of Hawi and arriving at Pololu Valley for a sunrise hike. Post hike coffee at the Kohala Coffee Mill. Afternoon surf at one of the spots near town. Lunch at King’s View Cafe. If you’re super fired up, an early evening bike ride on Kohala Mtn Road before Dinner at the Bamboo Restaurant. A mellower option is to spend the afternoon watching whales breach just offshore (Feb-April) and snorkeling one of the countless reefs in the crystal clear water.

Honor roll

Eats: Bamboo Restaurant, Kohala Coffee Mill, Kings View Cafe
Coffee: Kohala Coffee Mill

17. Big Sky, Montana

Photo: Seth Royal Kroft/Shutterstock

Perfect day

Spend a long, sunny day floating the Yellowstone catching trout, swimming off the boat, and working on a cooler of Moose Drool. Come winter, ski an uncrowded January pow day on Lone Peak. Either season, end the day with beers and mountain views on a deck.

Honor roll

Beers: Riverhouse deck in summer, Shedhorn Grill deck in winter, Big Sky Brewing
Eats: Lotus Pad for Thai food, By Word of Mouth for burgers
Coffee: Spur Coffee, buzz shakes at the Hungry Moose
Gear: GAS or Grizzly Outfitters in winter, East Slope or Gallatin River Guides for fishing
Music venue: Town Center stage for free Thursday night concerts

18. Santa Cruz, CA

Photo: stellamc/Shutterstock

Perfect day

In the water by dawn: Steamer Lane, the Hook, Pleasure Point, Natural Bridges. Shower off kelp slime and hit boozy brunch at Harbor Cafe. Afternoon nap followed by afternoon laps at UCSC MTB freeride trail and then go drive along the coast at sunset and check spots, or fly drones or something if the waves are blown out. Finish out the night nodding to indie rock or possibly corridos at The Catalyst.

Honor roll

Beers: Sante Adairius, Santa Cruz Mountain Brewing
Eats: Harbor Cafe
Coffee: Verve Coffee
Music venue: The Catalyst

19. Brevard, NC

Perfect day

Depending on water levels / hair-factor, do quick strikes on North and West forks of French Broad, or big mission on the Horsepasture or Toxaway. Other options include long play day on Section IV or just a day hike to check out waterfalls in Gorges State Park. Optimal conditions: warm bluebird day in late September after two nights of rain, the tulip trees are are yellow and the maples are starting to flame, and water temps are not yet cold. Head back to town for Mexican food blowout, beers, live bluegrass.

Honor roll

Beers: Oskar Blues
Eats: Quixote
Coffee: Bracken Mountain Bakery
Music venue: 185 King St

20. Fayetteville, WV

Perfect day

Wake up at the Gauley River (camp here) with vague memories of “fire jumping” at some point during the night before rain forced everyone into their tents. It’s a full on deluge now and under the kitchen tarp the crew is already talking about a triple crown run: the Lower Meadow down through the Upper Gauley, then a juicy late day run down New River Gorge. It’s your closeout to Gauleyfest, the best week of whitewater in the US, and never are you so proud to live on 40 mins away.

Honor roll

Beers: Pies and Pints
Gear: ACE Adventure Gear

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