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5 of The Most Charming Small Towns in America

I may call New York City home, but when I’m on vacation, I like to slow it down. You know– unplug a bit, maybe take a stroll down Main Street, park my rental car in a quiet surface lot for FREE(!). It’s the little things. Here are a few small towns in America I’m eying for my next vacation.

Healdsburg, CA

5 of The Most Charming Small Towns in America

Nestled in the Russian River Valley, this charming town is anything but podunk. The main square is flanked with incredible wine tasting rooms, gourmet cheese shops, stylish boutiques and more. Wine lovers will love sampling cabernets and zinfandels at Thumbprint Cellars (or Banshee Wines… or Portalupi Wines… really, there are a lot of tasting rooms to pick from). If all that pinot is making you hungry, check out the Parish Café for Cajun food, Mateo’s for upscale Latin fare, or Vallette for seasonal California cuisine. Though many places look fancy, locals will remind you this is a farming town. You can wear jeans and sneakers everywhere, kids are welcome in most places, and while the food and drink is incredible, no one takes themselves too seriously.

Galena, IL

5 of The Most Charming Small Towns in America

In the most northwestern corner of Illinois, you’ll find beautiful Galena. Founded in 1827, the historic downtown is filled with cute boutiques, perfect for a day spent bumming around. Not into shopping? Tour the former home of Ulysses S. Grant, the Dowling house (built in 1826, it’s the oldest home in town), or sign up for a historical walking tour. Outdoor enthusiasts will love hiking Horseshoe Mound, soaking up views of Illinois, Iowa and Wisconsin. And if you’re in the market for a little R&R, check out the Galena Day Spa. No matter how you spend your days, a dinner in town is a must. Try Fritz and Frites for a French bistro experience. Another favorite? The Log Cabin, which offers up that old school steakhouse vibe, complete with cozy lighting and live piano music.

Marfa, TX

5 of The Most Charming Small Towns in America

Texas is known for its vastness. And this little town (population: 1,800) is a long way from a major city—nearly a three hour drive to El Paso! Still, plenty of travelers flock to Marfa, and for good reason. It’s one of the most creative communities in the country. Love art? Check out the Chinati Foundation, a contemporary art museum with modern sculptures, installations, paintings and more. For an out of the ordinary stay, sleep in one of El Cosmico’s yurts or teepees. Outfitted with real, comfy beds, leather chair and couches, it’s about as far from roughing it as “camping” gets (though you will have to share a bathroom). Prefer accommodations with walls and an en suite? El Cosmico also rents out refurbished vintage trailers. Just take a look —they’re so cute! The hotel hosts many concerts, the biggest being the Trans-Pecos music festival. It’s perfect for music lovers who enjoy tunes under the big Texas sky.

Beaufort, SC

5 of The Most Charming Small Towns in America

Founded in 1711, this lowcountry harbor town is the perfect place for a long weekend. History buffs will have no shortage of places to explore, starting with the Old Sheldon Church ruins. This Greek Revival-style church, built in the 1740s, was burned down twice. What’s left is a stunning brick structure, surrounded old burial sites and oaks. Sounds weird, but it’s gorgeous. You can tour Penn Center, the first school for freed slaves, as well as numerous historic churches. Beaufort’s Visitor’s Center offers tons of information on how to best navigate the town’s historic landmarks. Water also plays a big role in the greatness of Beaufort. Personally, I love getting out on the water without getting in it. If you’re like me, you’ll love renting paddleboards or kayaks (and maybe even have a bottle nose dolphin sighting while you’re at it!). If you prefer less physical exertion, check out Captain Dick’s River Tour. You’ll learn a little bit about history, ecology and wildlife, all while getting out on the water.

Stowe, VT

5 of The Most Charming Small Towns in America

Though it is one of my favorite fall destinations, Stowe is a fantastic locale any time of year. Home of Mt. Mansfield, Vermont’s highest point, this small town offers plenty of outdoor adventures. Rent bikes and meander down the Stowe Recreation Path trail, which crosses the West Branch River on 11 old-style wooden bridges. Come winter, there’s lots of fantastic skiing (hey, there’s a reason they call it the Ski Capital of the East!). Stay and ski at Stowe Mountain Resort, the northeast’s only ski-in, ski-out luxury lodge. If hitting the slopes isn’t your thing, there’s no shortage of other ways to enjoy the outdoors. Try cross country skiing, snowshoeing, horseback riding (yes, even in the snow!), dog sledding, ice climbing or sign up for a snowmobiling excursion. For those who prefer to stay inside, harness your inner Ron Swanson and enroll in a woodworking course. Really, does it get much more Vermont than that?

What are some of your favorite small towns in America? Share in the comments!

I may call New York City home, but when I’m on vacation, I like to slow it down. Here are a few American small towns I’m eying for my next vacation.

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This Post Has 60 Comments
  1. My favorite small town is Fayetteville, West Virginia. On the edge of the New River Gorge National River with the best white water rafting in the world. The restaurants are all local creations, with my favorites being Cathedral Cafe and Pies and Pints.

  2. Favorite charming small towns

    Blowing Rock, NC
    Jerome, AZ
    Southport, NC
    Bluffton, SC
    Half Moon Bay, Ca

    Keep traveling!

  3. You have to visit Milford, MI. It has the best variety of restaurants, cute shops, Kensington Park for golf, hiking, biking, canoeing on the Huron River, concerts in Central park (much smaller than the original in NY).

  4. Eureka Springs, Arkansas, is like going back in time. Charming little city full of artists and wonderful unique shops. Lots of things to see and even a trolly ride to take you around town. Also some country western shows to make your trip complete!

  5. My favorite small town is my hometown and I’m lucky enough to work in a little B&B right in the town of Cornwall, New York (Hudson Valley). Its only an hour from NYC so we get a lot of weekend tripers. Also many people come from all over the world to visit the Storm King Art Center (outside museum). I actually had the privilege of meeting Samantha Brown about 10 years ago she came to Goshen, NY and spoke at Travel and Tourism Class. It was an honor meeting her.

  6. New Canaan, Connecticut – small quaint New England town of 19,000 – just a 1 1/4 hour train ride to Grand Central Station in NYC!

  7. Sam, I have watched you since “Girl Meets Hawaii” and I love all your shows. The BEST small town is Ashland, AL. Very quite but close to some amazing scenery! It’s also my hometown 🙂

  8. Winterset, IA, home of the Bridges of Madison County (or at least those that the locals haven’t burned down). Also, it’s the birthplace of John Wayne, his first house is a museum. Lovely parks in and out of town, and don’t forget to stop by Ken’s Restaurant. You saw it in the movie, it’s still there.

  9. Hammondsport, NY in the Finger Lakes region. Its perfect for a cup of coffee and a walk. Also fantastic antique shopping and nearby to some great wineries.

  10. Florence Alabama
    Great music, great downtown and great food. Plus right across the river is Muscle Shoals. Watch the documentary on Netflix called muscle Shoals. You’ll be glad you did

  11. Blue Ridge, Georgia is my hometown and a favorite place in Georgia for tourists. We have a scenic railroad, lake, mountain trails, festivals, lovely downtown, and a drive-in movie!

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5 Of The Most Charming Small Towns In America
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