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Where Should I Retire?

July 2, 2022, 2:32 p.m. EDT

We’re an outdoorsy family looking for a ‘funky’ town where we can eventually retire. Where should we go?

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By Silvia Ascarelli

Dear MarketWatch,

Where does a late-40s outdoorsy family with quirky kids move to with a long-term goal of retiring there?

I’m an operating-room nurse. As a family we are always outside hiking, mountain biking, camping, climbing, paddle boarding, skiing, etc. I’m looking for a funky, eclectic town with a small hospital for employment. 

We live in the San Francisco Bay Area. Funky and eclectic in our area used to be Berkeley, Santa Cruz and Fairfax. Most of those have been taken over by big tech. We like to be outside year round, and communities heavy on hiking, rock climbing and skiing tend to be funky towns.

Size-wise, we have lived in both big and small towns, and each has benefits. While we are on the West Coast, we are open to pretty much anywhere I can get an operating-room job as a nurse. 

We have equity in the home that we would sell and would like to own a place outright with a budget around $500,000-$600,000.

Thanks,

Scott

Dear Scott,

I can think of many outdoor places, though what’s funky is in the eye of the beholder. And as you note, they can lose that spirit. Some might say that has happened to Asheville, N.C., for example.

Unfortunately, even Bay Area housing values don’t mean you can easily buy in great outdoors towns. There just isn’t that much supply in many of the obvious places, and demand is high. So are prices. It’s going to be tough to find a home unless you are OK with a larger city or are open to less-obvious places. (Don’t worry, I’ve got some for you!) 

You’re likely already priced out of outdoor havens like Durango, Colo., and Hood River, Ore. 

Boulder, Colo., also is too pricey, and the new communities springing up nearby … well, don’t look for eclectic there.

If you do have your heart set on some of these places, think hard about how much space your family needs. A three-bedroom home may squeeze into your budget while a four-bedroom place does not, for example. 

And where on the priority list of outdoor activities is skiing? The frustrating search for affordable ski towns has been addressed a few times. If, for example, Salt Lake City or Ogden, Utah , meet your criteria, you could have amazing powder at well-known resorts within 90 minutes. Other city options with skiing nearby include Boise , Reno , Spokane and Grand Junction, Colo.  

Unfortunately, home prices in many of these areas have soared during COVID.

Read: Behold, the most overvalued housing markets in America

Instead, if downhill skiing can be just a weeklong family vacation, you can consider warmer outdoor spots like Chattanooga, Tenn. , and Bentonville, Ark . Since I hate to repeat myself, click on the links to read those articles.

Use the MarketWatch “Where Should I Retire?” tool to get county-level suggestions that meet your criteria. You can screen for hospitals, the weather, politics and many other factors that you haven’t mentioned but might be important to you.

I hope you’ll take the time to explore your list of finalists with short-term rentals that let you experience the community as a resident, not as a visitor. Do think about how much spectacular outdoors on your doorstep matters vs. the amenities of a larger town, whether what’s on supermarket shelves, ethnic cuisine, shopping options and concerts.

And be open to less-obvious suggestions. Here are three:

New Paltz, New York

Smack in the middle of New York’s Hudson Valley, this community of about 14,000 people is 90 miles from New York City and about an hour to the three main ski resorts in the Catskills (bigger ski resorts are about 3 hours away).

You’ll find some of the most technically difficult rock climbing in the U.S. at the Trapps and Near Trapps in the Mohonk Preserve , which you can reach using the River to Ridge Trail that begins at the edge of town. There’s plenty of opportunities for climbing, hiking , biking and water sports amid the thousands of acres of preserved open space, 90 miles of carriage roads and trails plus mountain lakes in the Preserve and nearby Minnewaska State Park, all part of the Shawangunk Mountains. 

You can also bike the mostly unpaved 24-mile Wallkill Valley Rail Trail , part of the bigger Empire State Trail , north to Kingston, and kayak in the Wallkill River.

More of that offbeat vibe comes from SUNY New Paltz and its 7,000 students. That keeps Main Street full of small, local shops. Indeed, New Paltz brags that it has no big box stores, nor are any just outside. (You can go to Poughkeepsie and Kingston for that.)

You’ll find farm-to-table restaurants, breweries, distilleries and fresh produce from area farms in New Paltz. The Culinary Institute of America’s restaurants , staffed by budding chefs, are a half-hour drive from New Paltz in Hyde Park, N.Y.

For those who want eclectic, plus more high-end dining, Woodstock, less than 30 miles north and closer to those ski options, may be the better choice. Yes, that Woodstock. 

If that’s you, you may need to look harder to find a home in your budget. 

Let’s talk work. From New Paltz, you have several possibilities: two hospitals are across the Hudson River in Poughkeepsie, reachable using the Empire State Trail when you don’t want to drive, and one is in Kingston.

As for travel, Poughkeepsie has train service to New York City. A handful of airlines fly from New York Stewart International Airport in Newburgh, less than 30 miles to the south. 

New Paltz has the mildest climate of my three suggestions: January highs average in the mid-30s. Summer highs are in the mid-80s. You’ll also have four months where you are likely to have a foot of snow.

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