Northern Shenandoah Guidebook

Tracy
Northern Shenandoah Guidebook

Sightseeing

Winchester-Frederick County Convention & Visitors Center
1400 S Pleasant Valley Rd
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Skyline Caverns
10344 Stonewall Jackson Hwy
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Luray Caverns
101 Cave Hill Rd
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Blandy Experimental Farm
400 Blandy Farm Ln
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Our endowed high school is a must see and a great photo op! Just a couple minutes drive from Fairmont house.
John Handley High School
425 Handley Blvd
Our endowed high school is a must see and a great photo op! Just a couple minutes drive from Fairmont house.
Just around the corner from the Fairmont house. Free tours are available.
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Handley Regional Library
100 W Piccadilly St
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Just around the corner from the Fairmont house. Free tours are available.
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Shenandoah University
1460 University Dr
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History & Museums

Winchester changed hands about 70 times during the civil war! Enjoy the Art, history, historic estates, beautiful gardens, hiking trails, live music, and more! Just a short walk or drive from Fairmont House.
Art, HIstory and more!
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Museum of the Shenandoah Valley
901 Amherst St
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Art, HIstory and more!
Revolutionary War fort Located almost directly behind the Fairmont house and an easy walk!
Historic Fort Loudoun Site
419 N Loudoun St
Revolutionary War fort Located almost directly behind the Fairmont house and an easy walk!
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Abram's Delight
1340 S Pleasant Valley Rd
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Belle Grove Plantation
336 Belle Grove Rd
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Cedar Creek & Belle Grove National Historical Park
7712 Main St
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Shenandoah Valley Civil War Museum
20 N Loudoun St
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George Washington spent a great deal of time in the Winchester area as a young man. His first elected office was to the House of Burgesses in 1755 representing Winchester.
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Washington's Office Museum
32 W Cork St
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George Washington spent a great deal of time in the Winchester area as a young man. His first elected office was to the House of Burgesses in 1755 representing Winchester.
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Kernstown Battlefield
610 Battle Park Dr
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Third Winchester Battlefield
541 Redbud Rd
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Patsy Cline Historic House
608 S Kent St
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Stonewall Jackson's Headquarters
415 N Braddock St
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Harpers Ferry National Historical Park
171 Shoreline Dr
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Long Branch Farm
Long Branch Lane
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Hollingsworth Mill
1360 S Pleasant Valley Rd
8 minute walk from Fairmont house
The Tomb Of Lord Fairfax
140 W Boscawen St
8 minute walk from Fairmont house

Restaurants & Pubs

Casual dining in the elegant George Washington hotel. Just minutes from the Fairmont House.
George's Food and Spirits
103 E Piccadilly St
Casual dining in the elegant George Washington hotel. Just minutes from the Fairmont House.
Elegant dining and fabulous cuisine. A five minute walk from the Fairmont house.
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Violino Ristorante Italiano
181 N Loudoun St
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Elegant dining and fabulous cuisine. A five minute walk from the Fairmont house.
My personal favorite! I think it’s some of the best food in Winchester.
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Oak Stone Craft Pizza and Bar
1000 Valley Ave
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My personal favorite! I think it’s some of the best food in Winchester.
Elegant dining and owned by the mayor of Winchester!
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Village Square Restaurant
103 N Loudoun St
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Elegant dining and owned by the mayor of Winchester!
Bonnie Blue Southern Market & Bakery
334 W Boscawen St
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Awabi Sushi Bar
111 S Loudoun St
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Great Mexican dining just a short walk from the Fairmont house in the middle of the old Towne Mall
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El Centro
1 N Loudoun St
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Great Mexican dining just a short walk from the Fairmont house in the middle of the old Towne Mall
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Taste Winchester History
149 N Loudoun St
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Union Jack Pub & Restaurant
101 N Loudoun St
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Chop Stick Cafe
207 N Kent St
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Roma Old Town Wood Fired Pizzeria
21 N Loudoun St
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164 N Loudoun St on the Old Town Mall
Ellie's Irish Pub Winchester
168 North Loudoun Street
164 N Loudoun St on the Old Town Mall
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Water Street Kitchen
2 S Loudoun St
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125 E Piccadilly St - Old Town Winchester
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Piccadilly's Public House & Restaurant
125 East Piccadilly Street
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125 E Piccadilly St - Old Town Winchester

Music

Enjoy variety variety love music from both local artists and international talents.
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Bright Box Theater
15 N Loudoun St
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186 N Loudoun St on the Old Town Mall. Check out FB listing: The Monument VA. Easy walk from the Fairmont House.
The Monument
186 North Loudoun Street
186 N Loudoun St on the Old Town Mall. Check out FB listing: The Monument VA. Easy walk from the Fairmont House.
Piccadilly's Public House & Restaurant
125 East Piccadilly Street
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Barns of Rose Hill
95 Chalmers Ct
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Valerie Hill Vineyard & Winery
1687 Marlboro Rd
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Coffee, Bagels & Lite Fare

An easy walk from the Fairmont house. Voted best bagels in downtown Winchester! Made fresh every morning!
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Steamy's Café
38 E Piccadilly St
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An easy walk from the Fairmont house. Voted best bagels in downtown Winchester! Made fresh every morning!
On the walking mall at the north end. 5 minute walk from Fairmont House.
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Espresso Bar & Cafe
165 N Loudoun St
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On the walking mall at the north end. 5 minute walk from Fairmont House.
A short drive but well worth the trip! Call your order in ahead for curbside service.
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Sclafani's New York Bagels and Bread
237 Kernstown Commons Blvd
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A short drive but well worth the trip! Call your order in ahead for curbside service.
Also on the walking mall at the south end.
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Hideaway Café
141 S Loudoun St
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Also on the walking mall at the south end.
Just a few minutes walk from the Fairmont house
Tropical Island Coffee & Cafe
39 W Piccadilly St
Just a few minutes walk from the Fairmont house

Wineries, Breweries & Cideries

The Wine Room at Taylor Pavilion
120 North Indian Alley
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Bear Chase Brewing Company
33665 Bear Chase Ln
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Just a short drive from the Fairmont house!
Misty Mountains Meadworks, Inc.
661 Warm Springs Rd
Just a short drive from the Fairmont house!
An easy walk from Fairmont House!
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Broken Window Brewing Co.
14 W Boscawen St
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An easy walk from Fairmont House!
Live music, lovely staff, nice wines and wonderful views!
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Valerie Hill Vineyard & Winery
1687 Marlboro Rd
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Live music, lovely staff, nice wines and wonderful views!
James Charles Winery & Vineyard
4063 Middle Rd
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50/50 Taphouse
29 W Cork St
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Old Town Cidery
326 North Cameron Street
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Winchester Ciderworks
2504 N Frederick Pike
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Winchester Brew Works
320 N Cameron St
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Won the silver metal in 2020 from The California Sommelier Challenge!
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Briede Family Vineyards
450 Green Spring Rd
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Won the silver metal in 2020 from The California Sommelier Challenge!
Breathtaking views from the blue ridge mountains looking west across the Shenandoah Valley
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Twin Oaks Tavern Winery
18035 Raven Rocks Rd
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Breathtaking views from the blue ridge mountains looking west across the Shenandoah Valley
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Veramar Vineyard
905 Quarry Rd
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Dirt Farm Brewing
18701 Foggy Bottom Rd
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B Chord Brewing Company
34266 Williams Gap Rd
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Alesatian Brewing Company
21 & 23 N Loudoun St
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Grocery, Wine & Beer

Turn Right out of the driveway at Fairmont house and just a little over a mile up the road on the right hand side
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Martin's Food
1950 S Pleasant Valley Rd
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Forgot something? Dollar tree is just up the road. Make a right out of the driveway and it’s near the Martin’s up the street.
Dollar Tree
180 Rivendell Ct
Forgot something? Dollar tree is just up the road. Make a right out of the driveway and it’s near the Martin’s up the street.