Surprisingly Unique, Outdoorsy, and Hip Cities and Towns

Even boondockers need a little city action sometimes. Below is a list of our favorite cities and towns in the US and Canada (that we’ve seen so far). The goal of this list is to call out cities or (better yet) towns with great outdoor and beer scenes that are lesser-known. Because of this, there are some notably great cities that aren’t on the list (Denver, CO, Austin, TX, Seattle, WA, Portland, OR, to name a few). I also focused on cities / towns I’ve spent time in. So I’m sure there are many that should be on this list, but aren’t. Enjoy!

Cities & Towns with a Great Outdoor & Beer Scene

Squamish, British Columbia

Squamish is just past Vancouver, about a three-hour drive from Seattle. It’s a small, but fantastic town that is well-known throughout the climbing and outdoor sports community. Allegedly it’s one of the top climbing and bouldering spots in the world since it’s home to The Chief, one of the largest granite slabs outside of Yosemite. There’s tons of hiking within and near Squamish (including the Mt. Garibaldi hike pictured below, which has the most stunning peak view I’ve seen), and lots of kayaking options in the crystal clear blue sea.

Squamish is absolute heaven for boondockers because the town is set up perfectly for people like us! We stayed for 2 weeks at various spots along a forest service road near The Chief (photos below). This road goes on for miles and miles and branches many different ways. There’s plenty of room for lots of boondockers, and cell service is great throughout most of the first 10 or so miles. There are also a number of clear glacial streams to bathe in, so you shouldn’t need to pay for a shower frequently!

There are a few good breweries in Squamish as well. Our favorites were: A Frame (I wear this hat constantly), Backcountry Brewing, and Howe Sound Brewing.

Mt. Garibaldi hike near Squamish, British Colombia.
Forest where we boondocked for two weeks in Squamish.
The Chief in Squamish, British Colombia.
Our favorite boondocking site in Squamish, British Colombia.

Seward, Alaska

Seward is one of the most stunningly gorgeous places I’ve ever seen. Patrick and I liked Seward so much that it’s one of the few places we plan to visit again when we return to Alaska. We both agreed we could live here (for the warmer months, at least). It’s a great mix of gorgeous hikes and parks, fantastic kayaking, and a good bar / nightlife scene when you need a break from physical activity. The water is so blue, and the flora / fauna so vibrant that it gives off a tropical vibe.

Kenai Fjords National Park is just outside the town, and it provides an endless amount of hiking and kayaking options – ranging from beginner in the Exit Glacier area, to advanced backcountry in the rest of the park. I believe you can kayak or hike to tidal glaciers in the park as well. You can boondock for free on the road leading out of the park. Cell service is great there. There’s an area called Miller’s Landing on one side of the town. It’s gorgeous (most photos below are from this area). You can pay to shower and do laundry there even if you don’t camp. You also can kayak or walk around from there for free.

There are a number of cool bars and breweries in Seward. Some of my favorites were: Seward Brewing – Breathtaking views from floor-to-ceiling second floor windows, and the brewery is covered in vintage snowboards. Unfortunately, I wasn’t impressed by the beer, but the ambiance was amazing (see below). Yukon Bar – This was an awesome spot with great local music on certain nights; Mexican food stand outside the brewery – This opens up after 9pm and has pretty incredible Mexican food. Definitely grab a late night bite here.

Seward Brewing Company.
View from Miller’s Landing in Seward, Alaska.
Harding Ice Fields in Kenai Fjords National Park, Alaska.

San Antonio, Texas

I was thoroughly, albeit unexpectedly, impressed with San Antonio. About an hour from Austin and on the outskirts of Texas hill country, this city has a little bit of everything and a truly unique vibe. For outdoor lovers, you have a 17 mile river path that follows the San Antonio river connecting many of the old missions, then extends into the city to sync with the famous Riverwalk, or ‘Venice of America.’ I ran a few miles of the path outside the city and loved it. It winds through numerous parks and lush, green scenery. There are lots of places to put-in a kayak and historical markers for points of interest. The Riverwalk in the city is gorgeous. Although the bars and restaurants along it are a bit of a tourist trap, they aren’t too over-priced, and the scenery and friendly ducks make it worth spending a few afternoons there.

For history / culture buffs, there’s a lot to see in San Antonio – from The Alamo and the other missions, to some of the oldest bars in the US. We checked out Menger Bar, which was a haunt of Teddy Roosevelt and the Rough Riders, and is said to be where he formed the gang. He and the Rough Riders also liked to frequent Buckthorn Saloon. Both bars date back to the mid-1800s.

There are tons and tons of breweries in San Antonio. We weren’t able to visit any because they weren’t open the days we were there, but we were able to try some of their beer at other venues. Other than breweries, we checked out Viva Tacoland, which was a really cool spot, and the St. Mary’s strip, which is an area of trendy, grungy, music-forward bars with an underground speakeasy vibe.

I wish we had more time in San Antonio. It’s high on my list of places I want to go back to.

Riverwalk downtown San Antonio, Texas. Source
Riverwalk downtown San Antonio, Texas. Source

Haines, Alaska

Similar to Seward, Haines was one of the most beautiful and unique places we’ve seen. We heard many people call Haines a ‘little slice of paradise.’ We were so enamored by it when we first arrived that we started looking at plots of land on the second day. It reminded me a bit of St. John’s – stunningly blue water that looks about as gorgeous as the Caribbean surrounded by lush, green, snow-capped mountains covered in a rainforest (a lot of southeastern Alaska is a temperate rainforest). The weather was perfect while we were there too – sunny and 70s every day. Haines is much smaller than Seward and most other towns on this list. There weren’t even many grocery options. However, there are a number of unique bars and bar/restaurants in the town, along with a brewery (although its beer wasn’t great). There are lots of kayaking and hiking options in the mountains and along the sea surrounding Haines. It’s also host of the Southeast Alaskan State Fair each July, which is one hell of a party.

Haines, Alaska.
Haines, Alaska.

Asheville, North Carolina

If great beer, loads of breweries, outdoor patios, live music, and really good food (including lots of good veggie options) are your thing, then you’ll love Asheville. It was the first stop on our truck camping journey, and we were tempted to stay much longer than planned! There’s great hiking in the Smoky Mountains surrounding Asheville, plus free boondocking on the Blue Ridge Highway. The city is hip, trendy, and filled with nothing but breweries. A few of our favorites were: Wicked Weed (and its Funkatorium), Archetype, Asheville Brewing, and Hi-Wire.

Evergreen, Colorado

Evergreen is a beautiful community about 30 minutes west of Denver. It’s tucked within the Rockies along Bear Creek. The landscape is mountainous, remote, and everything you’ve longed and hoped for in a Colorado adventure. The downtown has a historic Boardwalk that looks straight out of a movie (see below). There are lots of outdoor activity options because – hello – you’re in the Rockies, plus a few great bars and restaurants on the Boardwalk. This is one of our favorite places we’ve been in the Rockies.

The Boardwalk in downtown Evergreen, Colorado. Source.

Smithers, British Columbia

Tucked in gorgeous Bulkley Valley, in the shadow of Hudson Bay Mountain and surrounded by three mountain ranges, it’s no surprise that Smithers is a favorite stop for adventurers and outdoor enthusiasts. The downtown has an alpine theme, which has led it to be dubbed ‘Little Switzerland’ (see photos below). We found our favorite brewery in Canada during our brief stay in Smithers (Smithers Brewing).

Since the town is located along the Trans-Canadian Highway, you’ll meet many adventurers making the trek through Canada and Alaska there, plus find a number of free places around the city to boondock.

Smithers, British Columbia. Source

Whitehorse, Yukon

The Capital of the Yukon and nicknamed ‘Wilderness City,’ Whitehorse has a lot more going on than one might expect! It’s nestled on the banks of the Yukon River, surrounded by pristine lakes and rivers, and boasts a vibrant small city nightlife scene. We particularly liked Winterlong Brewery, and Woodcutter’s Blanket, a trendy cocktail bar that could easily hold its own amongst any cool spot in Logan Square or Bucktown, Chicago.

Whitehorse, Capital of the Yukon. Source 
Woodcutter’s Blanket (or ‘The Moose Bar’), Yukon, Canada. Source

Calgary, Alberta

Calgary was a shockingly cool city. We stopped by accident due to bad weather in Jasper / BAMF, but extended our stay because we liked it so much. Our of all places on this list, Calgary and Milwaukee have – in my opinion – the best breweries. Every brewery we went to in Calgary was incredibly unique, trendy, vivacious, and had truly excellent beer. A few of our favorites were: High Line (excellent IPAs), Cold Garden (one of the most wildly decorated, unique, and lively breweries I’ve ever seen), and Eighty Eight (everything you loved about the 80s/90s plus great beer). Cold Garden is located in Inglewood, which is a trendy brewery district in Calgary. There are lots of great walking / biking paths you can use to get around the city, plus Calgary is only an hour from BAMF and Jasper, which are two of the most popular Canadian parks and ski areas.

Eighty Eight Brewing Company Calgary, Canada. Source
Cold Garden Brewery Calgary, Canada. Source
Cold Garden Brewing Calgary, Canada. Source

Bozeman, Montana

Bozeman is a unique smaller city with an ‘up-and-coming’ vibe. We only stopped for a couple of days (and I was sick during it, so I wasn’t able to experience much), but we really liked the area. It’s surrounded by the Rockies – the Bridger Range is to the north, and the Spanish Peaks are to the south. Each have trails for hiking, biking, and skiing / snowboarding. There are lots of free natural places to camp near the city as well. The city itself is very trendy, yet has a quiet residential vibe. There are a number of cool coffee shops, breweries, restaurants, and bars. Again, I was unable to partake in much since I came down with a 103 degree fever partway through our first day there, but it was clear that this would be a great place to visit and live.

Ryun Sun Way Bozeman, Montana. Source

Fruita, Colorado

Fruita is a particularly neat place because it’s right on the border of Colorado and Utah, thus allowing you easy access to the Rockies of Colorado and the canyonlands of Utah. It’s a small community, but is known as one of the top mountain biking destinations in the world. It’s surrounded by the Colorado National Monument and various canyons (see below), and boasts a fun traveler / outdoorsy scene. Seriously, everyone there seems to partake in every possible outdoor sport. There are a couple of breweries in the city too: Suds Brothers, and Copper Club Brewing.

Colorado National Monument outside Fruita. Source

Milwaukee, Wisconsin

Milwaukee is a bit of a sleeper. You don’t expect it to be anywhere near as cool as it is. As I said above, Calgary and Milwaukee are my favorite beer cities. There isn’t a brewery I’ve tried in Milwaukee that I didn’t like… Not only are their beers great, but many offer cornhole / bags, darts, and other games. Some of our favorites are: Eagle Park Brewing, Good City Brewing, and Lakefront Brewery. During the summer, Milwaukee is one of the coolest US cities I’ve visited. Like Chicago, it boasts many miles of bike paths along the lakefront and a number of beaches. Unlike Chicago, however, the beaches are hip and trendy (not douchy), and the bike path goes through forests that contain beer gardens with outdoor games. We love this city. I could easily live here (in the summer).

Beer garden along bike path in Milwaukee. Source
Bradford Beach, Milwaukee. Source 

About the author

Lauren is a 'digital nomad' (for lack of a less obnoxious term) who works, lives, and travels out of her truck camper with her partner, Patrick, and dog, Odin, the one-eyed Wirehaired Pointing Griffon. She started TravelSages in the summer of 2013, and has since founded a digital marketing consultancy, called LyteYear, and a sustainability brand, called RePrint. Before moving into her tiny mobile home, Lauren lived in Chicago for 6 years, pursued two graduate degrees, studied abroad at Oxford, worked for a summer in Hong Kong, and traveled to various countries in between. She has a mildly unhealthy love of It’s Always Sunny in Philadelphia, Netflix, and breweries with good New England IPAs.

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