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Paia, maui, HI

The Most Active Cities in the U.S.

Is it really fair to list cities and towns in order and determine one winner? We think not. It’s better to celebrate all towns that offer access to adventure and exploration. In no particular order, this recurring feature will highlight a collection of those destinations to whet your appetite for a visit or even a relocation.

Bend, Oregon

Nestled between the Cascade Range to the west and the high desert to the east, Bend’s weather reaps the benefits of dry, low humidity summers and the snow-heavy Pacific storms of winter. Spend a little time cruising around town and it is strikingly obvious that the happy habitants of Bend know what they have and take full advantage of it. If there was a roof rack scale that determines a towns outdoorsy level, Bend would be off the chart.

The Dream

Get a job (part-time preferably) at Hydro Flask or Ruffwear or any one of the bazillion local startups that produce products born of their environment. Spend your summer surfing the wave at the Deschutes River whitewater park and hop a ski lift to bomb down mountain bike trails on the stratovolcano, Mount Bachelor. When the lifts are spinning and when the snow is flying, Bachelor has 3,365 feet of vertical drop and 101 trail runs for skiing and riding as well as a 22’ Olympic Superpipe.


Crux Fermentation Project, is Bend’s funkiest brewery, where the happy hour revolves around the sun with food and drink specials during the half-hour before and after sunset each day.

Paia, Maui, HI

Sitting on the north shore of the Hawaiian island of Maui, Paia (pronounced Pa-ee-a) is a wind and surf mecca with a classic beach town vibe. Check the forecast for any given day and let mother nature dictate which equipment in your ocean quiver gets the green light. The persistent trade winds which blow along the coast have made the north shore a destination for windsurfers from around the world for decades. And the surf, although far less notorious than the North Shore of Oahu, pumps through the winter months.

Although the large resort scene is on the leeward side of the island, tourists flock to experience the less commercialized town and pack the eateries and retail shops that are lined up in the one-block town.

The Dream

You may not have bussed tables in a restaurant since you first got your driver’s license but it has a new nobility when you’re refilling water for part-time resident celebrities like Woody Harrelson and Oprah. Saltwater will be gushing out of your nose from that pounding you took during a dreamy morning session in the ocean, while you are resetting tables. But it’s a reminder that ditching your job and belongings on the mainland was all worth it. 

A winter day with offshore, Kona winds and a building monster swell creates enough excitement for pro surfers to hop on flights from wherever to drop into a 40-foot wave at Jaws. When the trades kick back in, launch your kite and tear up the surf at Ho’okipa beach park. Or hop a shuttle to Maliko Gulch with your one-man outrigger canoe or standup paddleboard and ride the open ocean swells for 10 miles, downwind to Kahului Harbor. A double Maliko Run day may require a recovery day so take a drive on the Road to Hana and make a few stops for amazing waterfalls and hikes into the bamboo forest. Not making it the whole 2 hours on the slow and winding road to reach Hana town is totally acceptable. Remember, it’s not about the destination... 


Mama’s Fish House, tucked into a small oceanfront cove is an award-winning Polynesian restaurant that punches way above the simplicity of its name. The amazing service and atmosphere punctuate the world-class preparation of the fish caught only hours earlier. But don’t expect to roll in without a reservation or your whole paycheck. Mama’s is easily the busiest restaurant in Hawaii and among the most expensive.

Paia Fish Market gets the fish fresh off the boat too. Except you place your order at the counter, eat at the picnic tables and enjoy the people watching along the town’s only intersection. It’s super easy to find too. At the corner of Hana Hwy and Baldwin Ave, it’s the place with the line out the door.


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