There was a time when “Main Street” was the lifeline of a community and the center of social and economic life. As urban sprawl has taken over and suburbs have become the norm in many places, many of the best “Main Streets” in Virginia have all too often been lost in the shuffle.

In 1985, the Virginia Department of Housing and Community Development launched the Virginia Main Street Program in an effort to restore these essential community lifelines. Today, several decades years later, the program has adopted 25 communities, investing millions of dollars to revitalize downtown areas, preserve the historical architecture, and create jobs to boost local economies. Preservation Virginia, a non-profit organization dedicated to historic preservation in the state, reports that over ten thousand net new jobs have been created by Virginia Main Street businesses, over 3,000 net new businesses have formed and more than $1.2 billion has been invested, with the majority coming from the private sector.  The impact of these efforts is immense and nearly immeasurable in their ongoing impact. 

Here are some of the friendliest and most picturesque of Virginia’s Main Street communities (in alphabetical order) and why you won’t want to miss them. Do you agree that these are the best main streets in Virginia?

While we’ve listed 25 of the best main streets in Virginia, the truth is, there are many more that could rightly be added to this group. Do you have a favorite downtown, historic district, or main street in Virginia? If so, we would love to hear about them in the comments below!

For related content, be sure to check out our small town road trip.

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best main streets in Virginia

What are some other charming towns in Virginia?

As you might have gathered from reading our list of the best main streets in Virginia, the Old Dominion is positively brimming with charming and welcoming communities. Indeed, the small towns of Virginia are what give the state such personality and authenticity. No matter which region of the state you happen to visit, you'll want to plan to make a stop in a small town. Some of the most charming small towns in Virginia include Floyd, Charlottesville, Chincoteague, Smithfield, Cape Charles, Clarksville, Crozet, Scottsville, and Waterford. Learn more about these charming small towns to visit in Virginia.

What are the best day trips to take in Virginia?

If you're someone who enjoys taking day trips and embarking on adventures to explore your own backyard, Virginia won't disappoint. The Old Dominion offers so many great experiences without requiring much traveling. The following is a list of day trips in Virginia that will entertain just about anyone: Liberty Mills Farm, Chincoteague Island, Pippin Hill Farms & Vineyard, the Virginia Safari Park, Factory Antique Mall, Old Rag Mountain, the Sand Cave at Cumberland Gap Park, the town of Floyd, Harper's Ferry Adventure Center, and Luray Caverns. Learn more about these exciting day trips in Virginia.

What are some fun things to do in Virginia?

As mentioned above, visiting the Sand Cave at Cumberland Gap National Historic Park is one of the most memorable trips to take in Virginia. It's one of the most fun things to do in the state because it showcases a totally unexpected and otherworldly landmark. Because of wind and erosion, the sand cave has formed and measures over an acre and a half inside. Located near the Kentucky border, a trip to Virginia's very own sand cave is a must.