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Waynesboro Group Itinerary photo of patrons gathered around a bar by Cappy Phalen.

Nestled in the foothills of the Blue Ridge Mountains is the divinely placed mountain town of Waynesboro, Virginia, connecting ridge top vistas with the most flavorful local brews and downtown destinations. Round up your friends – this group-friendly itinerary will leave you cheering for more. You’ll find Waynesboro a perfect starting point for exploring both Skyline Drive and the northern end of the Blue Ridge Parkway.

Day 1: Explore the Blue Ridge Mountains

More than 500 miles of trail and 75 scenic overlooks await you along the Skyline Drive in the Shenandoah National Park, beginning a mere five miles from Downtown Waynesboro. Group photo destinations pair with family-size picnic areas, and in-park amenities provide the snacks, gear, and maps for all-day adventuring.

Alternatively, head south along the Blue Ridge Parkway and take in the offerings at Humpback Rocks, offering an interpretive Visitors Center, historic mountain farm, and a one-mile hike featuring 800’ of elevation gain and breathtaking summit views across the Shenandoah Valley.

Three flavors of local beer at Hops Kitchen sit atop a sandwich board with three brewery-style sandwiches.

Day 2: Drink In the Mountain Flavor

Follow-up on a day of adventuring with a brewery crawl along the Shenandoah Beerwerks Trail, where natural springs pump millions of gallons of artesian water to Basic City Beer Co’s award winning microbrews. Housed in a former brass foundry, they’re serving up live music, outdoor hammocks, and beer-infused cuisine in Hops Kitchen.

Multiply the flavors with additional visits to Blue Ridge Bucha, where their tap-room features handcrafted organic kombucha boasting a big taste and a small footprint. Barren Ridge Vineyards offers up elegant wines that are a pure reflection of the ancient and mineral rich soils of the Shenandoah Valley.

Patrons exit the brick-clad Wayne Theatre at night with streetlights glowing above baskets of blooming flowers.

Day 3: Walk through History

A downtown stroll connects interactive museums, historic sites, and live theatre performances for a day of cultural exploration. Begin at the Waynesboro Heritage Museum for nine galleries depicting the story of Waynesboro, including the railroad, traditional industries, and regional crafts. Stop by the P. Buckley Moss Gallery for the most extensive collection of the artist’s work, which draws inspiration from Virginia’s scenery, cultures, and traditions. Tour the Plumb House which, built in 1804, features period furnishings, a summer kitchen, and still-visible bullet holes from the last Civil War battle held in the Shenandoah Valley.

Finish the evening with live music or theatre performances at the lovingly restored Wayne Theatre Performing Arts Center, where a transformed 1920s vaudeville playhouse now welcomes touring musicians and musical productions.

Cruising for Cuisine?

These foodie destinations are perfect for large or small groups on the move:

  • Green Leaf Grill (small groups)
  • Farmhaus Coffee Co. (small groups)
  • Hops Kitchen
  • Waynesboro Farmers Market
  • Stable Craft Brewing