Small Town Trip Ideas & Itineraries

Small Town Trip Ideas & Itineraries

Virginia’s Main Street Communities and small towns are recognized for their down-home hospitality, locally-owned businesses, family-style eateries, heritage events and nearby unique outdoor attractions.

Add a small town to your Virginia itinerary or visit multiple to create a special multi-day tour experience. See how Virginia’s small towns can make a big impact on your next group tour.


– All about Staunton: Two Day Trip –


Voted one of “America’s Favorite Mountain Towns” by Travel + Leisure, Staunton is located in the heart of the Shenandoah Valley. The city’s charming downtown is home to a vibrant arts and music scene, local dining, and a cool array of independent shops and galleries clustered along the historic Main Street. Outdoor adventure and scenic drives, a night of theater, a step back in time at the Frontier Culture Museum, and more await you in this small town. Read more.


– Small Town Fans Can Stroll Smithfield: A “Park & Go” Getaway –Sunset on the Pagan River in Smithfield

​Genuine Smithfield exudes the charm and graciousness of bygone eras while maintaining its quaint river-town feel. Known worldwide for its famous ham curing process, the town also boasts a rich history, picturesque Main Street, and a vibrant arts scene. Smithfield’s historic district is the perfect “park & go” walking destination. Read more.


– Abingdon’s Historic Charm – Barter Theatre

Don’t just learn about history, experience it in the charming town of Abingdon. When you stroll down Main Street, you think about the Civil War soldiers involved in nearby battles who were treated by nurses on the grounds of what is now the elegant Martha Washington Inn & Spa. Enjoy a live performance at the historic Barter Theatre (group rates available). Read more.


– Group-Friendly Mountain Town Itinerary Scenic Skyline Drive

Take in breathtaking views along Skyline Drive or enjoy flavorful local brews along the Shenandoah Beerwerks Trail. Walk the streets of downtown Waynesboro and visit interactive museums and historic sites or see a live theatre performance. Round up your friends, this group-friendly itinerary will leave you cheering for more. Read more.


– By the Sea, by the Bay, by the Stars –

Assateague Island Lighthouse

Discover the spirit of Chincoteague Island with its unique island heritage, delicious food, shopping and beautiful neighboring Assateague Island for outdoor wonders, activities, and more! Visit the NASA Wallops Flight Facility Visitor Center, enjoy a pontoon cruise or take a leisurely beach stroll. Read more.


– Lose yourself in Louisa –

Take a peaceful escape to Louisa. Step back in time in this rural town while, at the same time, enjoying a multitude of modern experiences with a historical twist. Walk historic downtown Louisa and visit numerous historical landmarks, restaurants and shops. Take a break from the hustle and bustle and get lost in Louisa. Read more.


– Slip Away to Prince William –


Only a short drive from the nation’s capital, Prince William offers events and attractions for any kind of traveler. Stroll through the small town of Occoquan which features thriving artists, specialty gift shops and quaint restaurants, visit historic sites, enjoy a round of golf at pristine courses, sip wine with stunning views and more. Read more.


– Best of Lexington & Rockbridge: A Three-Day Tour –Natural Bridge Park

Visit one of the Seven Wonders of the World: The Natural Bridge at Natural Bridge State Park. Fun for all ages, nearby are the Caverns at Natural Bridge, Virginia Safari Park, Natural Bridge Zoo, and Dinosaur Kingdom II. Mix and match them to create your ideal afternoon of exploration. Enjoy tastings at local wineries and breweries. Take a carriage tour of historic Downtown Lexington and more. Read more.


– Fine Wines, Patsy Cline and Jefferson’s Design –

Downtown Winchester

Explore some of Virginia’s most charming small towns in this six day itinerary. Travel the fabulous Shenandoah Valley through scenic back roads and byways, stopping along the way to enjoy wineries, tour Patsy Cline’s home, and visit presidential homes including Thomas Jefferson’s Monticello, James Madison’s Montpelier and the Woodrow Wilson House. Read more.


– Wise County… Mountains, Music and MoreScenic Overlook in Wise

Offering a taste of the first “Old West” in a setting of mountain splendor on The Crooked Road, Virginia’s Heritage Music Trail, Wise is a music-lovers dream. Visit the home of Ralph Stanley, enjoy local wines or, if you are visiting on a Friday, check out local mountain music and dancing at Lay’s Hardware. Read more.


See more…
Suggested Trip Ideas
Virginia’s Small Towns: Three-Day Vacation Guide to Lynchburg

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