What to See, What to Do and Where to Stay in Winchester, VA

Weekend Getaways in Historic Cities of the East Coast 

Have you heard of Winchester in Virginia? Located at the tip of the Shenandoah Valley, a bit more than an hour inland from Washington, DC, this city’s historic old town makes for a splendid couple weekend getaway on the East Coast. Northern Virginia was at the forefront of the Civil War and this once-divided region welcomes visitors with open arms.

Winchester holds 250 years worth of history, including George Washington’s first public office, Stonewall Jackson’s headquarters and civil war battlefields, offering visitors a wide variety of things to see and do here. Not a history buff? The quaint old town of Winchester offers something for everyone! See for yourself…

This post is part of our “Weekend Getaway to Historic Cities on the East Coast” Series. This series of posts is aimed to highlight the role and significance that these cities had on the history of the United States while also offering some extra activities for couples to enjoy during a 2-3 day escapade. In our opinion, we’re providing a great mix of pleasure while taking in a bit of additional learning about the country.

Here’s what you will get from this post

Table of contents

Interesting museums are top of mind in historic cities of the East Coast and it’s no different in Winchester, VA. Although it may surprise you to also find an abundance of wineries, breweries, charming antique shops and artisan trails, all of which are within easy reach to fill your weekend escapade, providing a wide variety of activities to satisfy all types of travelers.

Marquestra Things to do in Winchester VA for couples

For your couples weekend getaway, in season activities can include a visit to the weekly farmers market, an evening at one of the last Drive-In movie theatres on the East Coast of the United States or a night out enjoying free outside concerts in the Old Town’s pedestrian mall. Read on, and you’ll quickly see why we recommend Winchester, VA as a perfect destination for a lovely weekend getaway for couples.

Disclosure: This post may include affiliate links for products and services that we use and recommend. If you purchase these through our website links, the price will stay the same to you and we get a percentage as a commission. 

The Old Town of Winchester

Marquestra Things to do in Winchester VA for couples

The shaded porches of the Georgian colonial-style homes with their traditional rocking chairs and lush gardens set the tone in this quiet and quaint section of the city of Winchester. Old Town Winchester will charm you with its pedestrian mall, historic buildings, museums and scenic walking trails. The mall itself has been welcoming visitors for over two centuries, it’s lined with traditional shops and restaurants, many with inviting outside patios.

In fact, it’s an ideal place to enjoy as a couple, for a weekend getaway, al the while taking advantage of the southern hospitality this state offers. We discovered this cute town while housesitting, an added benefit for the housesitter lifestyle

While you’re leisurely strolling through the pedestrian mall, stop in for an authentic shoe fitting experience at the Wilkins Shoe Center, Virginia’s largest independent family shoe store, owned and operated by three generations since 1947.

TIP: Download the Self-Guided Tour app such as Walking Washington’s Winchester

Farmers Market & Special Events

We admit having a soft side for farmers markets. Meeting local producers that are dedicated to providing us with fresh fruits and vegetables is always a pleasurable experience. Shop for fruits and produce, try to resist the artisan bread and cheeses, or don’t, and stock up!

The market has two locations along the pedestrian mall, the first is set up on the Old Courthouse lawn on Thursdays (June thru August, 11 am to 2 pm) and on the weekend at the Taylor Pavillon on Saturdays (May thru Sept, 9 am to 1 pm)  Visit oldtownwinchesterva.com/old-town-farmers-market/

Marquestra Things to do in Winchester VA for couples

The Old Town farmers market’s size is modest but the over all region has many other offerings. The beautiful surrounding countryside, valley and mountain range was once considered the breadbasket of the Confederate army, as it’s rich with the land’s bounties. Furthermore, Winchester holds many special events throughout the year, the most famous one being the Shenandoah Apple Blossom Festival. With parades, a carnival fair and fun rides, this special event makes for an entertaining weekend getaway for couples as well.

Did you know that this whole area is considered the apple capital of the world?  A heritage which most likely began because of the requirement, on the deed of sale, that 100 winter apple trees are planted by the buyer of a parcel of land sold from future President George Washington to the Frederick County.

Marquestra Things to do in Winchester VA for couples

Photo Credit ~ Shenandoah Apple Blossom Festival (R)

TIP: Enjoy the Apple Blossom Festival in Spring and the Winchester Craft Beer Week in June. Other regional events: Virginia Cider Festival in July Wine & Food Festival in September.

Marquestra Things to do in Winchester VA for couples

Crowds fill Old Town for the Hop Blossom Festival

Museums & Historic Sites

No state has more Civil War history than Virginia and Old Town Winchester lives up to this with no shortage of historic sites and museums. From visiting George Washington’s first office to modern day Patsy Cline’s humble family home, Old Town is packed with war remembrance, history, art and an abundance of stories.

Museum of Shenandoah Valley:

Learn more about the local people’s heritage with a self-guided tour or if you’re lucky enough, get insights from friendly volunteers like Bill, a war veteran eager to share his wealth of war history and regional knowledge with you.

Interesting fact: The takeover of the Federal arsenal in the Shenandoah Valley by John Brown, an abolitionist from Kansas, was one of the catalyst battles that lead to the civil war.

Marquestra Things to do in Winchester VA for couples

The MSV of Shenandoah Valley is set on 214 acres of land, it’s home to the Glen Burnie house, the 6th generation landlord. It also boasts magnificent gardens featuring a variety of outdoor exhibits as well. The gardens are also an ideal romantic venue for weddings and celebrations in addition to hosting the popular Gardens at Night outside concert series which are held on summer weekends, just bring your lawn chair and enjoy the music. In the museum’s main building, view artefacts from the civil war period and Mr Lee Thompson’s fabulous collection of miniatures doll houses, his lifetime passion.

Marquestra Things to do in Winchester VA for couples

This is not a full scale room, it’s a miniaturized one… Incredible work!

Marquestra Things to do in Winchester VA for couples

We viewed the Lego Brick Sculptures from artist Sean Kenney at the MSV, a tremendous display of creativity.
A must see if you visit before labor day 2018.

The Shenandoah Valley Civil War Museum:

This modest museum is set in the historic Georgian-style courthouse on Loundoun Street. You’ll find over 3000 artifacts, like lead bullets, swords and pieces of uniforms from the Civil War, most found on the nearby battlefields of Winchester. The building was also used as a holding cell for prisoners of both sides of the war. You can witness the original graffiti left from many of them on the plaster walls along with several pictures of soldiers, many too young, posing before battle. Allow for a 30-45 minute visit. Admission is $5.

Marquestra Things to do in Winchester VA for couples

Insider Tip: Want to learn more about the Civil War? You can find many interesting leaflets and maps about the Shenandoah Valley Battlefields in the main lobby or here…

Patsy Cline Historic House:

Get a glimpse of the simple and modest home of this iconic Country star by touring her family’s tiny house in which she lived for longer than anywhere else during her lifetime. The admission fee includes the guided tour. General Admission $8 / Seniors $6. Length of tours – 30 minutes, which allows for the guided tour, photo ops and gift shop.

View more museums and sites to visit in Old Town Winchester 

Marquestra Things to do in Winchester VA for couples

Enjoy the Fresh Air

With all of the beautiful surroundings this region offers, you can enjoy many scenic walks. Just make sure to bring a good pair of walking shoes as Winchester, VA, offers a multitude of walking trail options with some passing through Old Town.

Walk on the many trails of  the Green Circle :

The trails of the Green circle are meant to connect areas of history with nature. Passing through Glen Burnie Historic House & Gardens (Museum of the Shenandoah Valley), Old Town Winchester, the Jim Barnett Park, Shenandoah University and the Abrams Creek Wetlands Preserve where you can view an abundance of wildlife and birds. Follow the trail sections’ green signs and remember, the trail is also shared by cyclists, hikers and joggers. View the trails here…

Marquestra Things to do in Winchester VA for couples

Coming soon at the MSV:

With 214 acres, the MSV area is the largest green space in the city. The museum and its other buildings only take up a portion of it and nearly 90 acres as the rest remains as pastures, wetlands and forest. The new park in the City of Winchester will feature three miles of trails winding through beautiful wooded areas, fields and natural setting, all free of charge. Artwork is presented through peaceful nature surroundings throughout the trail, which includes bridges and a boardwalk. A perfect opportunity for couples and family alike to enjoy art and wildlife while taking a leisurely stroll. To date, 2.5 million dollars has been raised for the trails project.

Insider Tip: If you enjoy hiking, head over to the Shenandoah Valley Park, only 30 minutes away, with miles of accessible hiking trails in addition to the Appalachian Trail that passes right through it.

Local Artists & Antiques

Enjoy the beautiful countryside and discover an abundance of creative folks along the Virginia Artisan Trail. On the first Saturday of the month, hit the trail and visit some of the 58 sites, including local studios, galleries and farms. As you wander about the trail, tours, live demonstrations and special exhibits offer a fantastic opportunity to meet with artists and producers. Year-round in Winchester, Frederick and Clarke counties.

Go Antiquing:

With such history, Winchester, VA, offers a bountiful treasure trove throughout the county. Start at Blue Peacock Antiques in Old Town Winchester, a 40 vendor coop under one roof with an endless array of spectacular finds. Make sure to keep some space in the car to bring back that irresistible find!

Marquestra Things to do in Winchester VA for couples

Drive In Cinema:

One of the last remaining old-style drive-ins on the East Coast of the USA, the Family Drive-In movie theater still shows double features on summer evenings. Pack some chairs in the trunk and arrive early to enjoy a good old Saturday night at the movies. Celebrating its 40th anniversary, we caught a classic showing of “Grease” on one of two outdoor screens, how fun is that? Note: There’s a well appointed snack bar with lots to choose from, but if you decide to bring outside food and beverages, a $5 fee is applied on arrival.

Marquestra Things to do in Winchester VA for couples

Enjoy a glass or two at a brewery or winery

Regardless of the fact that you’re a beer or wine drinker, the Winchester region will provide you and your taste buds with many delightful options. The Old Town area is home to a few craft breweries in addition to the 50/50 Taphouse which offers a selection of 50 local brews on tap. These breweries will satisfy any beer enthusiast but if you’re more into wine, an array of award-winning wineries and even some distilleries can all be experienced, less than an hour away by car.


Escutcheon Brewing Company: Check their Facebook page for regular live music events 
Alesatian Brewing Company  Second floor beside the pizza place on the pedestrian mall
Broken Window:  The best red Ale
Winchester Brew Works 

Marquestra Things to do in Winchester VA for couples


Head to the Skyline Drive, which happens to be the entrance to the Shenandoah Valley for a great tour of Northern Virginia wineries around Front Royal. There are simply too many to name, but here are a few recommendations that make for a great afternoon driving loop from Old Town Winchester.

If you like single malts, why not begin your wine tour with a dram of whiskey? Not exactly the expected start for a wine tour but the extra 15-minute drive from the Front Royal region to Sperryville will reward you at the Copper Fox Distillery. Home of Wasmund’s single malt whiskey, this detour is worth your while. Tucked away at the end of a little country road and nestled by a brook, this mixture of hipster – vintage meets country vibe venue is proof that when there’s a will there’s a way… To whiskey!

The Copper Fox compound includes an antique shop and also an onsite brewery. Opening hours, tours and whiskey tastings: www.copperfox.biz
View more distilleries to visit here…

Marquestra Things to do in Winchester VA for couples

A quaint little brook runs through the back of the distillery

Insider Tip:  If you’re exploring this great region, plan an amazing dining experience at Patrick O’Connell’s notorious Inn at Little Washington, a 2-star Michelin restaurant in this area. Ready to splurge? Why not stay at this Relais Chateau, 5 stars, 5-diamond property for an exceptional escapade you’ll both remember for years to come.

Second stop Rappahannock Winery & Didas Distillery:

Acres of vines welcome you to this beautiful winery, a founding estate in the region. This 15-year-old establishment is the recipient of many wine-making awards, find out why by tasting the fruit of their labor, 6 samples for $10. You can also indulge in a second tasting room, their newly added distillery offering, featuring brandy, gin and vodka.

Marquestra Things to do in Winchester VA for couples

Carrying on at Chester Gap

At 1000 feet in elevation, this vineyard offers a wonderful selection of delectable wines and one if not, the most spectacular view of the region. Plan for an end of the afternoon visit and enjoy the last rays of the day, as the sun sets in the valley. On the way home, visit Valerie Hill Vineyard & Winery   It’s grand Manor house is over two centuries old with Live music in the gardens in season. Otherwise, you can attend special events such as history and haunting tours ($).

Marquestra Things to do in Winchester VA for couples

1000 ft elevation gets you this spectacular view

See Other Regional Wineries That You Can enjoy at www.virginiawine.org

Another great way to spend the afternoon is to have High Tea at Historic Rosemount Manor: 

Indulge in a traditional fare of delicious pastries, scones and dainty sandwiches at this fabulous venue while having tea overlooking the gorgeous gardens.  Why not book a room for a romantic getaway at their B&B

Where to Stay in Winchester VA

The city of Winchester has many hotel chains to pick from in its vicinity and here are a few of the top reviewed hotel in the area we’ve selected for you.

Luxury: 10 miles (20 min) out from Historic Winchester along the country roads you’ll find the magnificent top rated and award winning L’Auberge Provencale. The Inn has an on-site restaurant and its location near the Skyline Drive is ideal for exploring the region. A truly exceptional treat for a couples weekend getaway.  Another recommendation close to town is the romantic The Inn at Vaucluse Spring.

Mid-range: These two options are perfectly situated to enjoy the Old Town.
The George Washington – a Wyndham Grand Hotel – offers a great value with inside pool, free parking and a beautiful outside patio.
The Old Waterstreet Inn B&B. Federal style brick home welcoming guests with generous full breakfast.
Pembroke Springs Retreat, a Japanese style B&B in a beautiful mountain setting with traditional spring-fed Japanese baths.

Budget: The Hampton Inn has the best reviews in the economy range and the best bang for your buck. Guest get free breakfast and can enjoy the outside pool.

If camping is more your style, you can hook your RV or pitch a tent at Candy Hill Campground or Cove Campground.

Get the Latest Reviews and Prices for Winchester Hotels Here

Photo Credit ~ L’Auberge Provencale

Photo Credit ~The George Washington a Wyndham Inn Hotel

Marquestra Things to do in Winchester VA for couples WHERE TO STAY

Photo Credit ~The Hampton Inn

Where to Eat in Winchester VA

No weekend getaway would be perfect without some spectacular places to eat and relax with your partner and loved one. While we didn’t get to eat out as often during our housesitting assignment here are a few local recommendations.

Village Square Piano Bar: Right on the pedestrian mall, enjoy the raw bar delicacies or the outside patio.
La Niçoise French restaurant, a local recommendation for traditional French cuisine.
Water Street Kitchen: Down home cooking. Opt for the roasted Brussels Sprout with Bacon side dish, just delish!

We truly enjoyed our three weeks in the region and never expected that there were so many things to do in Winchester, VA for couples. Sometimes you just stumble in on of these places, almost kept secret by the locals, as if hoping to preserve it all to themselves.

So we’re spreading the news, Winchester, Va is a great place for a fabulous couples weekend getaway, come to see for yourselves.

Have you been to Winchester, VA?
Please share your experiences with us, comments or questions below…

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What to See, What to Do and Where to Stay in Winchester, VA. Located at the tip of the Shenandoah Valley, a bit more than an hour inland from Washington, DC, this city's historic old town of Northern Virginia makes for a splendid couple weekend getaway on the East Coast. #thingstodoinwinchesterva #winchesterva #weekendgetawayeastcoast #historiccity
Things to do in Winchester, Va for Couples. What to See, What to Do and Where to Stay in Winchester, VA. Located at the tip of the Shenandoah Valley, a bit more than an hour inland from Washington, DC, this city's historic old town of Northern Virginia makes for a splendid couple weekend getaway on the East Coast. #thingstodoinwinchesterva #winchesterva #weekendgetawayeastcoast #historiccity