The Quirky Guide to Hipster Asheville, NC

The Quirky Guide to Hipster Asheville, NC

Asheville is just one of those places you keep hearing about over and over again until finally you say !enough! – I’ll go and check it out.  Thankfully one of my wonderful digital friends lives in Asheville and actually invited me to speak at her annual conference, giving me zero excuses to come and check out this famously funky city.  Researching before the trip gave me visions of the weird things to do in Austin, so when I landed into the city’s teeny-tiny airport, I was ready and braced for whatever the hipster had in store for me.

I LOVED Asheville and to repeat something my good friend Margo says, “every time I go to Asheville, I end up wanting to move there.”  But why?  Here’s my quirky, hipsterish guide to some fun things to do in Asheville, NC.

The Urban Trail


Downtown Asheville is very compact, easy to get around, and best seen on foot – how else will you decide which of the many bars, pubs, cafes, shops, restaurants, alleyways, parks, and street performers will get your undivided attention?

One suggestion I have for you is to start with the Urban Trail – an unmarked path, but there are maps at the Visitor’s Center – that walks you through some of the city highlights, like the public art, the popular city park pictured above, known as “Splashville.”  Take note of Pritchard Park, which you’ll want to revisit on Friday night for the famous Asheville drum circle.

An alternative to walking is to take the La Zoom Comedy Tour (ticket booth at Battery Park & Haywood).  It’s a huge purple bus that drives you around town.  It’s one of the most popular tours in town, though honestly I found it frustrating to discern which things were true and which were fictional parts of the show. (However, looking for  a fun thing to do in Asheville with kids? One of the La Zoom tours would be a good bet.)


Asheville also has some incredible architecture.  A few noteworthy stops:

  • The Church of St Lawrence: has one of the largest unsupported domes in the country.  Go inside and you’ll think you’re in Europe, not North Carolina.
  • Grove Arcade:  like elsewhere on the east coast, this fabulous old building has hung on for dear life, and has managed to make a grand revival.  Pictured above, the building now has several great restaurants and cafes, as well as a mish-mash of shops.  Opened in 1929, taken over by the government for decades, and now a fashionable city icon, pay this building some respect – it deserves it.
  • The Homes of Montford: You’ll need a car for this one (though the La Zoom tour does give you a flavour), but in the Montford district, you’ll see some of the most grandiose homes in North Carolina.  This used to be a weathy enclave, hence the building spree, and subsequent residences always had the good sense to take care of things.
  • Asheville City Hall and Buncombe County Corthouse: These two “skyscrapers” (note the sense of irony), Art Deco and Neoclassical respectively, are the most picturesque parts of the skyline.   Both were built in the late 1920s, and thankfully survived a severe depression that hit the city right afterwards.

The Biltmore Estate

The Biltmore Estate really needs no introduction, as it’s probably one of Asheville’s most famous attractions.  But a trip here is really one of the most fun things to do in Asheville NC, because there’s so much going on.  After a winding drive of a couple of miles, this amazing manor home appears out of the forest – a quirk intentionally designed to give the building, which is the largest private residence in the world, a lot of “wow” factor. (It works.)  But what to do once you’re here?

  • You can tour the main family home, which includes some fantastic views and priceless artworks inside.
  • Relax a bit after that with  free wine tasting , either with or without a tour of the winery.  Lots of good wines here – and you can buy on site to take back to your hotel for sipping, or to pack away for souvenirs.
  • How about having some ice cream from the on site creamery?  This is a must.
  • Last but not least, there are also tours and excursions out into the managed forest that surrounds the estate.  Biking, boating, Land Rovers, Segways, and all sorts of things are options.

Make sure that one day of your trip is reserved exclusively for a visit to Biltmore.  When you check in at the ticket desk, be sure to review the map and have the guides suggest to you the best route for your day – with a lot of ground to cover, it is best to have a plan.

Boutique Shopping

Downtown Asheville has a LOT of quirky, hipsterish, fun and funky shops.  With names like Funky Mutt and Chocolate Fetish, you’ll have just as much fun window shopping as you will actually stocking up on souvenirs and personal purchases.  It’s next to impossible to make recommendations, but a few places that did catch my eye:

  • Malaprop’s: consistently rated as one of the best bookstores in the country.  Can’t turn that down, right?
  • Woolworth Walk: the largest gallery in Asheville showing exclusively local artists, with an old fashioned soda fountain/ice cream parlour inside.  Need I say more?

All of these shops are right in the heart of downtown.  But why don’t you take a walk and see what strikes your fancy?


It’s hard to think that you’d ever want to leave Asheville, but there are options for daytrips if you’re looking to see some of the amazing mountain countryside that surrounds the city.  A few recommendations:

  • Waterfalls and Hikes near Brevard: Heading west and south to the South Carolina border, you’ll hit Brevard, surrounded with some of the best known waterfalls in the state, including famed local swimming pond Looking Glass Falls (pictured above), as well as my fave, Whitewater Falls, one of the tallest falls on the east coast.
  • Blue Ridge Parkway:  some say this is one the best drives in America, and the route skirts just outside of Asheville, so why not check it out?  This parkway has limited access points, so be sure to plan your route so you know how you’ll be getting back to Asheville.
  • Chimney Rock Park: also another great outdoor wonder, has some great height to the trails (so these are probably more difficult than others in the area), but the views are also superb.

Where to Stay

After so many fun things to do in Asheville NC, one needs some beauty sleep!  But where to rest your weary feet?

  • The Grove Park Inn: This is definitely a ‘splurge’ choice, though they often have special offers.  The Grove Park has the best view in town (pictured above), and one of the best spas in the country.  A few miles outside of downtown.
  • For a central downtown experience, the Renaissance Hotel is a great choice.  Lots of hospitality, good amenities, and the location is quiet but just a couple blocks to the attractions.
  • A Montford B&B:  As mentioned above, Montford is a hotbed for architecture, and many of these homes are now B&B’s.  How about the 1900 Inn?
  • You can also spend the night at the Biltmore!

Be sure to stay tuned – coming up soon is our Foodie’s Guide to Asheville!. Come hungry :-)

Have you been to Asheville?  What are your tips for fun things to do in Asheville NC?


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