Staunton, Virginia Shines Bright with Arts, Culture & Cocktails

3-Day Itinerary for Staunton

Nestled in the heart of the Shenandoah Valley, Staunton, Virginia, is a charming destination brimming with rich history, vibrant culture, and scenic beauty. This meticulously curated itinerary offers a glimpse into the city’s unique blend of old-world charm and contemporary attractions. From exploring the birthplace of President Woodrow Wilson to strolling the bustling streets lined with boutique shops and delectable dining options, Staunton promises a delightful and immersive travel experience for every kind of adventurer.

OxEye Staunton tasting room

Enjoy These Staunton, VA Attractions and More:

Frontier Culture Museum
Woodrow Wilson Presidential Library and Museum
Virginia Scenic Railway
American Shakespeare Center
Trinity Episcopal Church
Sunspots Studios
Ciders From Mars
and plenty more!

Get More Staunton, Virginia Travel Info and Subscribe for FREE

Frontier Culture Museum in Staunton, Virginia

Staunton, Virginia DAY-TO-DAY ITINERARY

DAY 1 – Things to Do in Staunton, VA

Staunton is one of the oldest cities west of the Blue Ridge Mountains. Step back in time at the living-history Frontier Culture Museum to learn about the daily life of the region’s earliest settlers.

Next, discover the life and legacy of the country’s 28th president in the city where he was born at the Woodrow Wilson Presidential Library and Museum. An exclusive ‘Behind-the- Scenes” guide tour provides a fuller picture of his complex life and legacy.

Love nostalgic rail journeys? Set aside three hours to relax and sightsee aboard the Virginia Scenic Railway, round-trip excursions depart twice daily (Thursday-Sunday).

Downtown Staunton, VA

DAY 2 – Staunton, Virginia Attractions

Shakespeare is serious fun at the American Shakespeare Center. So is the Blackfriars Playhouse Tour, where you’ll go on-stage, behind the stage, and even under the stage as guides tell the story of England’s first indoor theater and describe how the staging conditions of 17th-century London shaped the works of Shakespeare and his fellow playwrights.

Art enthusiasts are invited to step inside Gothic-Revival Trinity Episcopal Church and marvel at 12 Tiffany stained glass windows, which date from 1898-1936. Contemporary artworks are produced daily via live glass-blowing demonstrations at Sunspots Studios. Interested in acquiring original works from regional artists? The CoArt Gallery and the R.R. Smith Center for History & Art display some of the best. The Depot Grille is a popular restaurant housed in a historic train station. The restaurant offers a unique dining experience with a cozy and inviting atmosphere. The Depot Grille is known for its delicious American cuisine, featuring a variety of dishes ranging from steaks and seafood to sandwiches and salads.

Buckingham Branch Railroad in Staunton, Virginia

DAY 3 – Staunton, VA Activities and More

For something truly memorable, opt for a masterclass in cheese and wine in a beautifully restored tasting room. Ballerino Creamery’s head cheesemaker Louella Hill and master vintner John Kiers of Ox-Eye Vineyards join forces to help you taste your way through the Valley’s freshest flavors.

Pick up a copy of the self-guided walking tour and get acquainted with Staunton’s preservation success; six historic districts are independently listed on the National Register of Historic Places.

Refresh yourself at the Ciders From Mars taproom, where you can enjoy a full flight or a single glass of their flagship Hellas Dry Cider. It’s made with a blend of modern and heirloom apples, grown locally. BLU Point Seafood Co. showcases lobster rolls and seafood baskets, as well as catches straight from the Chesapeake Bay such as rockfish, blue crab, and oysters. Private dining areas can accommodate groups of up to 80 people. Gorgeous mountain scenery surrounds Staunton. Two national parks, Shenandoah National Park and the Blue Ridge Parkway are close by and make an easy destination for sunset views.