Northern Shenandoah Guidebook
Sightseeing
Winchester-Frederick County Convention & Visitors Center
1400 S Pleasant Valley RdSkyline Caverns
10344 Stonewall Jackson HwyLuray Caverns
101 Cave Hill RdBlandy Experimental Farm
400 Blandy Farm LnOur 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 BlvdOur 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.
14 locals recommend
Handley Regional Library
100 W Piccadilly StJust around the corner from the Fairmont house. Free tours are available.
Shenandoah University
1460 University DrHistory & 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.
Museum of the Shenandoah Valley
901 Amherst StArt, HIstory and more!
Revolutionary War fort Located almost directly behind the Fairmont house and an easy walk!
Historic Fort Loudoun Site
419 N Loudoun StRevolutionary War fort Located almost directly behind the Fairmont house and an easy walk!
Abram's Delight
1340 S Pleasant Valley RdBelle Grove Plantation
336 Belle Grove Rd
Cedar Creek & Belle Grove National Historical Park
7712 Main StShenandoah Valley Civil War Museum
20 N Loudoun StGeorge 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.
23 locals recommend
Washington's Office Museum
32 W Cork StGeorge 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.
Kernstown Battlefield
610 Battle Park DrThird Winchester Battlefield
541 Redbud RdPatsy Cline Historic House
608 S Kent StStonewall Jackson's Headquarters
415 N Braddock StHarpers Ferry National Historical Park
171 Shoreline Dr
Long Branch Farm
Long Branch LaneHollingsworth Mill
1360 S Pleasant Valley RdThe Tomb Of Lord Fairfax
140 W Boscawen St8 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 StCasual 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.
15 locals recommend
Violino Ristorante Italiano
181 N Loudoun StElegant 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.
13 locals recommend
Oak Stone Craft Pizza and Bar
1000 Valley AveMy personal favorite! I think it’s some of the best food in Winchester.
Village Square Restaurant
103 N Loudoun StElegant dining and owned by the mayor of Winchester!
Bonnie Blue Southern Market & Bakery
334 W Boscawen StAwabi Sushi Bar
111 S Loudoun StGreat Mexican dining just a short walk from the Fairmont house in the middle of the old Towne Mall
16 locals recommend
El Centro
1 N Loudoun StGreat Mexican dining just a short walk from the Fairmont house in the middle of the old Towne Mall
Taste Winchester History
149 N Loudoun StUnion Jack Pub & Restaurant
101 N Loudoun StChop Stick Cafe
207 N Kent StRoma Old Town Wood Fired Pizzeria
21 N Loudoun St
Ellie's Irish Pub Winchester
168 North Loudoun Street164 N Loudoun St on the Old Town Mall
Water Street Kitchen
2 S Loudoun St
Piccadilly's Public House & Restaurant
125 East Piccadilly Street125 E Piccadilly St - Old Town Winchester
Music
Enjoy variety variety love music from both local artists and international talents.
Bright Box Theater
15 N Loudoun St186 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 Street186 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 StreetBarns of Rose Hill
95 Chalmers CtValerie Hill Vineyard & Winery
1687 Marlboro RdCoffee, Bagels & Lite Fare
An easy walk from the Fairmont house. Voted best bagels in downtown Winchester! Made fresh every morning!
9 locals recommend
Steamy's Café
38 E Piccadilly StAn 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.
8 locals recommend
Espresso Bar & Cafe
165 N Loudoun StOn 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.
9 locals recommend
Sclafani's New York Bagels and Bread
237 Kernstown Commons BlvdA short drive but well worth the trip! Call your order in ahead for curbside service.
Hideaway Café
141 S Loudoun StAlso on the walking mall at the south end.
Tropical Island Coffee & Cafe
39 W Piccadilly StJust a few minutes walk from the Fairmont house
Wineries, Breweries & Cideries
The Wine Room at Taylor Pavilion
120 North Indian AlleyBear Chase Brewing Company
33665 Bear Chase LnMisty Mountains Meadworks, Inc.
661 Warm Springs RdJust a short drive from the Fairmont house!
Broken Window Brewing Co.
14 W Boscawen StAn easy walk from Fairmont House!
Live music, lovely staff, nice wines and wonderful views!
26 locals recommend
Valerie Hill Vineyard & Winery
1687 Marlboro RdLive music, lovely staff, nice wines and wonderful views!
James Charles Winery & Vineyard
4063 Middle Rd50/50 Taphouse
29 W Cork StOld Town Cidery
326 North Cameron StreetWinchester Ciderworks
2504 N Frederick PikeWinchester Brew Works
320 N Cameron StWon the silver metal in 2020 from The California Sommelier Challenge!
7 locals recommend
Briede Family Vineyards
450 Green Spring RdWon the silver metal in 2020 from The California Sommelier Challenge!
Breathtaking views from the blue ridge mountains looking west across the Shenandoah Valley
32 locals recommend
Twin Oaks Tavern Winery
18035 Raven Rocks RdBreathtaking views from the blue ridge mountains looking west across the Shenandoah Valley
Veramar Vineyard
905 Quarry Rd
Dirt Farm Brewing
18701 Foggy Bottom Rd
B Chord Brewing Company
34266 Williams Gap Rd
Alesatian Brewing Company
21 & 23 N Loudoun StGrocery, 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
Martin's Food
1950 S Pleasant Valley RdForgot 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 CtForgot 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.