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Best of Winchester Guide

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Winchester
Sitting at the northernmost corner of Virginia in the Shenandoah Valley, Winchester offers visitors the chance to explore historical sites, museums, vineyards, farmers' markets, and tree-lined Old Town streets once wandered by the likes of George Washington and Stonewall Jackson. The fruitful fields of the surrounding Frederick County have earned the area the title "apple capital of the world," with the city hosting the Shenandoah Apple Blossom Festival annually for almost a century.

All things to do » Things to do

Rocking S Ranch
Rocking S Ranch
Attraction type: Ranches
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Museum of the Shenandoah Valley
Museum of the Shenandoah Valley
Owner description: The Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley. This regional history complex includes a house... more Owner description: The Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley. This regional history complex includes a house dating to the eighteenth century, six acres of spectacular gardens, and a 50,000-square-foot museum featuring changing exhibitions, a permanent display of miniature houses, and an expansive gallery exploring the history and decorative arts of the Shenandoah Valley. The MSV also includes a Museum Store and café (admission not required). The galleries are open year-round; the house and gardens April through October. The MSV sits on land originally claimed by Winchester founder James Wood in 1735. The property was passed through generations of Wood and Glass families until being acquired by Wood descendant and MSV benefactor Julian Wood Glass Jr. (1910–1992) between 1952 and 1955. Glass and his partner at the time, R. Lee Taylor (1924–2000), worked together to transform the site and its Glen Burnie House—built in 1794 by James Wood’s son Robert—into a country retreat where the couple entertained in high style. less
Attraction type: Art Museums; History Museums
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Stonewall Jackson's Headquarters
Stonewall Jackson's Headquarters
Season: Open Daily April 1 to October 31
Attraction type: History Museums; Specialty Museums
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Shenandoah Valley Discovery Museum
Shenandoah Valley Discovery Museum
Owner description: Our mission at the Shenandoah Valley Discovery Museum is to ignite creativity, spark curiosity and inspire learning in visitors of all ages by providing a rich variety of... more Owner description: Our mission at the Shenandoah Valley Discovery Museum is to ignite creativity, spark curiosity and inspire learning in visitors of all ages by providing a rich variety of interactive, hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts.All exhibits, activities and experiences provided by the Discovery Museum adhere to the following philosophical guidelines:Exhibits, activities and programs are interactive, participatory and informal, and give visitors opportunities to experiment, have fun playing, use their imaginations and share ideas.Visitors are engaged at their own level of expertise and experience.Activities and programs are multi-sensory, authentic, honest, and factual.The Museum works in a spirit of cooperation and partnership with educational, cultural, governmental and community organizations. less
Attraction type: Science Museums; Educational sites; Children's Museums
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Handley Regional Library
Handley Regional Library
Attraction type: Libraries; Points of Interest & Landmarks
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All places to eat » Places to eat

Coach & Horses Tea Room
Coach & Horses Tea Room
Ranked #1 of 295 Restaurants in Winchester
Price: $14 - $27
Cuisines: American, International, British
Good for: Business meetings, Families with children, Romantic, Local cuisine, Large groups, Special occasions
Dining options: Lunch, Brunch, Dinner, Late Night, Accepts American Express, Accepts Discover, Accepts Mastercard, Accepts Visa, Cash Only, Digital Payments, Free Off-Street Parking, Free Wifi, Parking Available, Private Dining, Reservations, Seating, Takeout, Waitstaff, Wheelchair Accessible
Neighborhood Italian Kitchen
Neighborhood Italian Kitchen
Ranked #2 of 295 Restaurants in Winchester
Cuisines: Italian, Pizza
Good for: Families with children, Kids, Local cuisine, Special occasions
Dining options: Lunch, Dinner, Delivery, Highchairs Available, Parking Available, Reservations, Seating, Serves Alcohol, Takeout, Waitstaff, Wheelchair Accessible
Violino Ristorante Italiano
Violino Ristorante Italiano
Ranked #3 of 295 Restaurants in Winchester
Price: $15 - $30
Cuisines: Italian
Good for: Business meetings, Families with children, Romantic, Special occasions
Dining options: Lunch, Dinner, Full Bar, Outdoor Seating, Reservations, Seating, Serves Alcohol, Waitstaff, Wheelchair Accessible
Roma Old Town Wood-Fired Pizzeria
Roma Old Town Wood-Fired Pizzeria
Ranked #4 of 295 Restaurants in Winchester
Price: $9 - $20
Cuisines: Italian, Bar, Pizza
Good for: Families with children, Kids, Large groups
Dining options: Lunch, Dinner, Late Night, Full Bar, Outdoor Seating, Seating, Serves Alcohol, Takeout, Television, Waitstaff, Wheelchair Accessible
Taqueria Guadalajara
Taqueria Guadalajara
Ranked #5 of 295 Restaurants in Winchester
Cuisines: Mexican, Latin, Spanish
Good for: Families with children, Kids, Special occasions
Dining options: Lunch, Dinner, Accepts American Express, Accepts Discover, Accepts Mastercard, Accepts Visa, Full Bar, Parking Available, Reservations, Seating, Serves Alcohol, Takeout, Television, Waitstaff, Wheelchair Accessible, Wine and Beer

All accommodations » Where to stay - Budget

Nearby recommended accommodations:

Holiday Inn Express Winchester South
2.5 of 5
Holiday Inn Express Winchester South
$96 - $124
Ranked #1 of 2 Hotels in Stephens City
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All accommodations » Where to stay - Midrange

Country Inn & Suites By Carlson, Winchester
3.0 of 5
Country Inn & Suites By Carlson, Winchester
$87 - $140
Ranked #1 of 25 Hotels in Winchester
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The George Washington A Wyndham Grand Hotel
3.5 of 5
The George Washington A Wyndham Grand Hotel
$109 - $209
Ranked #2 of 25 Hotels in Winchester
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Wingate by Wyndham Winchester
2.5 of 5
Wingate by Wyndham Winchester
$109 - $154
Ranked #3 of 25 Hotels in Winchester
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Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.