7 Hip Virginia Towns for the Urban Minded Millennial

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For a lot of folks, there’s nothing quite like the city. Urban destinations from New York to DC are becoming increasingly appealing to creative people of all stripes, and particularly for the younger crowd. People love having on-hand access to great food and cultural experiences, and many are willing to pay a high price in rent, space, and overall comfort to do so.

Still, there’s something to be said for the small town experience. Though many a Millennial might be quick to write off setting up shop in a town on the countryside over a the city on the horizon, not all towns are the sleepy hallows that people believe them to be. More and more young urbanites are looking to small towns to start a family and buy a home, but they’re often afraid of leaving behind the fast paced lifestyle the city offers.

Thankfully, plenty of smaller towns are also home to vibrant, colorful communities with thriving economies, shopping districts bustling with trendy artisan shops, and hopping late night bar strips. The great state of Virginia is fortunate enough to have many towns that match that very description. And furthermore, home prices in Virginia are on par with the national average and growing, making a home a great way to settle into an investment. These are the ones that top our list of great small Virginia towns for the city slicker at heart:


One thing Virginia isn’t short on is beauty, and Charlottesville has it in spades. Home to the historic and iconic University of Virginia, Charlottesville is surrounded by breathtaking mountains and countryside, and is consistently voted as Virginia’s top town. However while Charlottesville may have small town charm, this city of 43,000 is anything but sleepy. Charlottesville is home to Broadway shows, festivals, concerts, and “The Corner,” a fun district near UVa, is packed with energetic bars, restaurants and stores. And with connections to the D.C. Metro and regional Amtrak, calling Charlottesville home is a winning proposition.

Arlington/ Alexandria

Arlington is the second principal city in the D.C. metro area, though it’s technically an unincorporated county and not an independent city. It features tons of high-paying employment, high safety, strong home values, and some of the best overall schools in the nation. According to Livability.com, it’s ranked 3rd in the top 100 places in the US to live. Combined, the cities of Arlington and nearby Alexandria are ranked as #1 and #3 for young adults by USA Today. Located only 7 miles from downtown D.C., amazing food, amazing culture, and a well known artistic community make Alexandria a true hotspot.

Glen Allen

Urban convenience at a small town pace is what you’ll find in Glen Allen. Voted the best city in Virginia to raise a family, Glen Allen is affordable, peaceful, and still offers urban entertainment. 3 Fortune 500 companies are located in Glen Allen, and when its residents aren’t enjoying local shops and restaurants, they’re relaxing in the open air in beautiful spaces like Crump Park for outdoorsy adventures.


Blacksburg is the home of Virginia Tech, and was cited by Businessweek as being the best college town in the South. Blacksburg is a center for high tech and research which boosts the local economy without making it unaffordable. The cost of living here is 7% less than the national average. As the college town of a nationally renowned school, there’s always more than enough to do and see in Blacksburg.

Big Stone Gap

Big Stone Gap is the hip mountain town without the mountains. Within the same mold as towns like Asheville, North Carolina or Oxford, Ohio, Big Stone Gap is a progressive town with plenty to experience. This small town of only 5,600 is home to many festivals including the popular Gathering in the Gap music festival. Picturesque to a T, good shopping and good food is also an important part of the Big Stone Gap experience.


CNN recently named Chincoteague the 2nd coolest small town in America . . . and for good reason. Famous seafood, excellent beaches, and an easy going, laid back experience is the order of the day here. This small fishing town of nearly 3,000 features a full-on mid-Atlantic appeal. Crabbing, clamming, boat tours, and kayaking are all popular activities as is the abundance of fun local stores. Chincoteague is a place people love to live in as much as they love to visit.


Any list of Virginia destinations would be incomplete without its capital. Richmond is undoubtedly more of a city than a small town, but at only a hundred thousand people it’s no New York, Chicago, or Atlanta—and that’s a good thing. Richmond has more in common with a town than it does with an urban center, and it certainly feels that way when you walk the streets. Still, a major financial and business center, Richmond has all the advantages of a city. It’s recently renovated River District is where you’ll find an ecliptic and unabashed nightlife along the canal walk. Not a city to shy away from boozy treats, Richmond is home to at least 12 microbreweries and a number of other wineries and distilleries. Many of its restaurants have been named in the top 100 in the South. Named the 3rd best city for business by Marketwatch and located 98 miles from DC and easily accessible on regional rail, Richmond is one capital worth living in.