Plan Your Trip
Travel Tools for a Seamless Shenandoah Valley Experience
Are you planning to travel—or already traveling—through the Shenandoah Valley? Whether you’re winding your way down the Blue Ridge or hopping between historic towns, there’s always something just around the bend.
To make it easy, we’ve divided the Shenandoah Valley into two regions: North Shenandoah Valley and South Shenandoah Valley.
Each offers its own unforgettable mix of landscapes, experiences, and charm. Use one of the itineraries below to explore— no matter where you are, North or South Shenandoah Valley, you’ll never be more than an hour away from your next adventure.
Click on the interactive map to select a curated itinerary to explore.
North Shenandoah Valley
History, Gardens & Easy Adventure
for Older Adults
Day 1
Winchester Wonders
- Morning tour of the Museum of the Shenandoah Valley
- Lunch in Old Town Winchester with café seating
- Visit Abram’s Delight or explore the gardens
- Stay at The George Washington Hotel
Day 2
Countryside Drives & Covered Bridges
- Scenic drive through Shenandoah County
- Visit Meems Bottom Covered Bridge
- Midday tasting at Muse Vineyards
- Dinner at Edinburg Mill Restaurant
Day 3
History & Culture in Clarke County
- Tour Long Branch Historic House & Farm
- See demos of grain grinding at Burwell-Morgan Mill & Picnic from Locke’s Store
- Enjoy Garden Audio Tours at the State Arboretum of Virginia
- Have afternoon tea at The Tea Cart in Berryville
Big Fun in the Big Outdoors
Fun for Families
Day 1
Caverns & Curiosity
- Tour Luray Caverns (stalactites + antique car museum)
- Lunch at the café or nearby diner
- Afternoon splash in the Hawksbill Greenway Park
- Stay in a riverside cabin or family-friendly lodge
Day 2
Water Adventures & Wildlife
- Morning tubing trip with Shenandoah River Outfitters
- Afternoon visit to Skyline Drive for a short kid-friendly hike
- Dinner in Front Royal, ice cream on Main Street
Day 3
Farm Fun & Farewell
- Visit a working farm in Shenandoah County with animals or u-pick berries
- Connect with your inner child at Dinosaur Land and Applewood Raceway
- Stop at a farmers market or bakery before heading out
Northern Shenandoah Valley, Elevated
for Adventure Seekers
Day 1
Summit & Sip
- Sunrise hike to Stony Man Summit via Skyline Drive
- Late morning coffee in Front Royal
- Afternoon kayaking or rafting on the Shenandoah River
- Dinner + drinks in a restored downtown warehouse
Day 2
Paddle & Pour
- Morning bike ride on Hawksbill Greenway or forested back roads
- Tour and tasting at Wisteria Farm & Vineyard
- Explore Downtown Luray galleries or grab a local beer
- Stay in a treehouse, yurt, or boutique cabin
Day 3
Berryville & Beyond
- Brunch at L’Auberge Provençale or Cordial Coffee
- Hike the Appalachian Trails
- Bike Cool Spring Battlefield Trails along the Shenandoah River
- Cheers at Chilly Hollow Brewing Company
South Shenandoah Valley
Uninterrupted Beauty & Cultural Charm
for Older Adults
Day 1
History & Arts in Staunton
- Explore the Woodrow Wilson Presidential Library & Museum
- Lunch on Beverley Street at a historic café
- Get the perfect shot the Camera Heritage Museum
- Matinee show at the American Shakespeare Center
- Dinner at Zynodoa (farm-to-table, elevated Southern cuisine)
Day 2
Garden Walks & Scenic Drives
- Drive the Blue Ridge Parkway, stopping at overlooks
- Visit Andre Viette’s Garden Center or a lavender farm in Waynesboro
- Wine tasting at Barren Ridge Vineyards
- Evening at The Blackburn Inn or quaint B&B in Lexington
Day 3
Lexington’s Legacy
- Morning carriage tour of downtown Lexington
- Visit Virginia Military Institute Museum
- Browse local galleries before departing
Easy-Going Escapes for Every Generation
Fun for Families
Day 1
Harrisonburg Highlights
- Breakfast at a downtown diner
- Visit Explore More Discovery Museum for young kids
- Stroll through the Edith J. Carrier Arboretum
- Dinner at Jack Brown’s or Grilled Cheese Mania
Day 2
Resort Fun & Family Thrills
- Head to Massanutten Resort for Waterpark fun (indoors or out), ziplining, mini golf or a scenic chairlift ride
- Picnic lunch or dine at the Summit
- Evening s’mores at your cabin or suite
Day 3
Underground Wonders & Sweet Treats
- Tour Grand Caverns in Grottoes
- Stop at Smiley’s Ice Cream or a roadside stand on your way home
Thrill & Chill in the Southern Shenandoah Valley
for Adventure Seekers
Day 1
Peaks & Pour-overs
- Morning hike at Humpback Rocks, House Mountain or Natural Chimneys Regional Park
- Lunch and tasting flight at Devils Backbone Outpost Tap Room
- Walk the mural trail in downtown Waynesboro or fall in love with St. Mary’s Falls
- Overnight at a glamping site or boutique inn
Day 2
Paddle & Pour
- Kayak or SUP on the Maury River in Buena Vista
- Late lunch at Pure Eats or Heliotrope Brewery
- Sunset wine tasting at Rockbridge Vineyard
- Stargazing in Natural Bridge State Park
Day 3
Brunch & Browse
- Sunday brunch in Staunton
- Stop by artisan markets or antique shops on your route home
North Shenandoah Valley
History, Gardens & Easy Adventure
for Older Adults
Day 1
Winchester Wonders
- Morning tour of the Museum of the Shenandoah Valley
- Lunch in Old Town Winchester with café seating
- Visit Abram’s Delight or explore the gardens
- Stay at The George Washington Hotel
Day 2
Countryside Drives & Covered Bridges
- Scenic drive through Shenandoah County
- Visit Meems Bottom Covered Bridge
- Midday tasting at Muse Vineyards
- Dinner at Edinburg Mill Restaurant
Day 3
History & Culture in Clarke County
- Tour Long Branch Historic House & Farm
- See demos of grain grinding at Burwell-Morgan Mill & Picnic from Locke’s Store
- Enjoy Garden Audio Tours at the State Arboretum of Virginia
- Have afternoon tea at The Tea Cart in Berryville
Big Fun in the Big Outdoors
Fun for Families
Day 1
Caverns & Curiosity
- Tour Luray Caverns (stalactites + antique car museum)
- Lunch at the café or nearby diner
- Afternoon splash in the Hawksbill Greenway Park
- Stay in a riverside cabin or family-friendly lodge
Day 2
Water Adventures & Wildlife
- Morning tubing trip with Shenandoah River Outfitters
- Afternoon visit to Skyline Drive for a short kid-friendly hike
- Dinner in Front Royal, ice cream on Main Street
Day 3
Farm Fun & Farewell
- Visit a working farm in Shenandoah County with animals or u-pick berries
- Connect with your inner child at Dinosaur Land and Applewood Raceway
- Stop at a farmers market or bakery before heading out
Northern Shenandoah Valley, Elevated
for Adventure Seekers
Day 1
Summit & Sip
- Sunrise hike to Stony Man Summit via Skyline Drive
- Late morning coffee in Front Royal
- Afternoon kayaking or rafting on the Shenandoah River
- Dinner + drinks in a restored downtown warehouse
Day 2
Paddle & Pour
- Morning bike ride on Hawksbill Greenway or forested back roads
- Tour and tasting at Wisteria Farm & Vineyard
- Explore Downtown Luray galleries or grab a local beer
- Stay in a treehouse, yurt, or boutique cabin
Day 3
Berryville & Beyond
- Brunch at L’Auberge Provençale or Cordial Coffee
- Hike the Appalachian Trails
- Bike Cool Spring Battlefield Trails along the Shenandoah River
- Cheers at Chilly Hollow Brewing Company
South Shenandoah Valley
Uninterrupted Beauty & Cultural Charm
for Older Adults
Day 1
History & Arts in Staunton
- Explore the Woodrow Wilson Presidential Library & Museum
- Lunch on Beverley Street at a historic café
- Get the perfect shot the Camera Heritage Museum
- Matinee show at the American Shakespeare Center
- Dinner at Zynodoa (farm-to-table, elevated Southern cuisine)
Day 2
Garden Walks & Scenic Drives
- Drive the Blue Ridge Parkway, stopping at overlooks
- Visit Andre Viette’s Garden Center or a lavender farm in Waynesboro
- Wine tasting at Barren Ridge Vineyards
- Evening at The Blackburn Inn or quaint B&B in Lexington
Day 3
Lexington’s Legacy
- Morning carriage tour of downtown Lexington
- Visit Virginia Military Institute Museum
- Browse local galleries before departing
Easy-Going Escapes for Every Generation
Fun for Families
Day 1
Harrisonburg Highlights
- Breakfast at a downtown diner
- Visit Explore More Discovery Museum for young kids
- Stroll through the Edith J. Carrier Arboretum
- Dinner at Jack Brown’s or Grilled Cheese Mania
Day 2
Resort Fun & Family Thrills
- Head to Massanutten Resort for Waterpark fun (indoors or out), ziplining, mini golf or a scenic chairlift ride
- Picnic lunch or dine at the Summit
- Evening s’mores at your cabin or suite
Day 3
Underground Wonders & Sweet Treats
- Tour Grand Caverns in Grottoes
- Stop at Smiley’s Ice Cream or a roadside stand on your way home
Thrill & Chill in the Southern Shenandoah Valley
for Adventure Seekers
Day 1
Peaks & Pour-overs
- Morning hike at Humpback Rocks, House Mountain or Natural Chimneys Regional Park
- Lunch and tasting flight at Devils Backbone Outpost Tap Room
- Walk the mural trail in downtown Waynesboro or fall in love with St. Mary’s Falls
- Overnight at a glamping site or boutique inn
Day 2
Paddle & Pour
- Kayak or SUP on the Maury River in Buena Vista
- Late lunch at Pure Eats or Heliotrope Brewery
- Sunset wine tasting at Rockbridge Vineyard
- Stargazing in Natural Bridge State Park
Day 3
Brunch & Browse
- Sunday brunch in Staunton
- Stop by artisan markets or antique shops on your route home
Discover the Valley’s Heritage
Historic & Cultural Tours
Day 1
Civil War & Beyond
- Visit New Market Battlefield & Museum
- Walk historic downtown Winchester – Civil War Trails, Old Town shops
- Stay at a historic inn or period-themed B&B
Day 2
Presidential & Artistic Heritage
- Tour the Woodrow Wilson Presidential Library in Staunton
- See a matinee at the American Shakespeare Center
- Dinner at a locally owned tavern with 18th-century roots
Day 3
Black Heritage Trail
- Explore Harrisonburg’s NE community trail and museums
- Visit small-town historic Black churches or cemeteries along the Valley
Valley by the Mile
Scenic Routes
Day 1
Northern Valley
- Start in Winchester, enjoying the Museum of the Shenandoah Valley
- Drive south along Route 11 (“The Old Valley Pike”) stopping in Strasburg & Edinburg
- Overnight in Shenandoah County, enjoy mountain-view dining
Day 2
Middle Valley Meander
- Visit Mount Jackson and Woodstock Tower for views
- Stop at family-run wineries and antique shops
- Continue south to Harrisonburg for dinner and live music
Day 3
Southern Peaks
- Drive through Rockbridge Baths and Brownsburg
- Take a detour to Goshen Pass or Natural Bridge
- End in Lexington with a historic walking tour