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Virginia’s Shenandoah Valley: The seven best attractions for Boomers

Written By | Jun 9, 2019
Virginia's Shenandoah Valley

Meems Bottom covered bridge in Virginia’s Shenandoah Valley. Image via

SHENANDOAH VALLEY, Va. Attention Boomers. Thinking of visiting the Shenandoah Valley this summer? You’ll be happy to know this vast, picturesque locale is only a short 1 1/2 hour drive from Washington Dulles International Airport. The airport straddles Fairfax and Loudoun Counties, home to Northern Virginia’s fast-growing D.C. suburbs.

Perhaps you’ll want to start your vacation by enjoying the city life in Washington for a couple days. But the, you can slow your pace by heading west on U.S. Route 50, or via the Dulles Greenway and Virginia Route 7. You’ll soon wind up in Virginia’s beautiful Shenandoah Valley, which meanders southward, bounded by the contours of the Blue Ridge Mountains to the East and the Appalachians to the West. Interstate 81 offers the most efficient way to get from locale to locale once you’ve arrived in the area. Once you get there, you’ll soon see that natural wonders, unusual attractions, and excellent food and wine destinations beckon.

That’s a lot of territory. To simplify your journey, here’s our guide to 7 must-do Boomer-centric destinations to experience once you’re there!

Veramar Vineyards

This winery, located in Clark County, Virginia’s Shenandoah Valley region has it all: breathtaking views, delicious wines and a heartwarming story. Roughly 55 miles northwest of Washington, D.C., you can reach it easily by traveling West on Virginia Route 7 heading toward Winchester. Once you climb up and over the Blue Ridge Mountains at Bluemont, you’ll be heading right back down and into the Shenandoah River Valley. After crossing this usually quiet and picturesque river, keep your eye out for a left-turn sign for Veramar. That’s your first stop on your Shenandoah Valley Boomer tour itinerary.

Jim and Della Bogaty, who own and operate the vineyard and winery were married within days of meeting one another. At the time, Jim was in the navy and was due to ship out soon. The couple honeymooned on a boat named Veramar. So naturally, decades later, when they opened a winery they named it in memory of that memorable event.

veramar vineyards in shenandoah valley is a good stop for baby boomers

Make sure to put this award wining winery on your list of stop when you visit the Shenandoah Valley

When you arrive at the winery, just belly up to the bar and sip on a delightful flight of wines. Or pick a glass and sit outside taking in the majestic views of the countryside. Or taste the flight and pick a favorite to savor. The vineyard is open daily at noon. Check out the Veramar website for particulars, including hours and special events.

The Taste Winchester History Tour
food tour in shenandoah Valley

This food tour will leave you satisfied from both delicious bites as well as the history of Winchester, Virginia!

Not far west from Veramar, you’ll arrive in the historic mountain town of Winchester, Virginia on the Northern edge of the Shenandoah Valley.

If you decide to use Winchester as your touring base, you absolutely need to do the Winchester food tour put on by food lovers Misty and Anthony Weaver. As with most food tours, this one is so much more that just food with a bit of history built in. Though your tour remains within Winchester’s pedestrian-friendly downtown “walking mall,” you’ll love the different spots and care with which each one was chosen. Prepare yourself the way you would for your annual physical if possible: no eating for at least 12 hours prior.

Some of the tour’s highlights: Fresco Kitchen, where special attention is given to gluten free and other dietary restrictions. Hard to believe their delicious rolls were Gluten Free.

Also, the German Table will delight with their take on Germany’s underground secret: curry wurst. Perhaps you can cajole the owner to bring out her special selection of beers to wash down your meal. We don’t want to spoil all the surprises along the way. But you will definitely get your money’s worth and more on this food tour.

Cost of the tour is $55 per person. For more information, click this link.

Patsy Cline Museum
patsy cline museum virginia

Here’s the modest home of Patsy Cline, located in Winchester, part of the Shenandoah Valley

Also in Winchester, you can visit the Patsy Cline home and museum.

Though legendary country singer Patsy Cline might be a music legend, she wasn’t always a favorite in her Virginia hometown of Winchester, Virginia. That might be because Ms. Cline hailed from the poorer side of town. Even after her phenomenal success in the music world, it was two decades after her tragic early death that Virginia even acknowledged she was a native daughter. Nonetheless, her home is now preserved as a museum and is open for tours. See the living room where she learned to play piano and the dining room. This dual purpose area hosted both family meals and a drawing desk where Patsy herself designed her own outfits for performances.

Tickets to the museum are $8 and the house is open daily from 9 am to 7 pm. Here’s the link.

Box Office Brewery
box office brewery in Shenandoah valley boomer trip

You’ll want to see the beautiful architecture that has been preserved in this historic building in the Shenandoah Valley

Craft beer lover or not, you have to appreciate the time and love that went in to renovating this old theatre located in Strasburg, Virginia. This colorful mountain town is not too far South from Winchester, via the generally speedy I-81.

Karl Roulston and Tom Price, the team behind Box Office Brewery had no idea what they were getting into when they purchased the abandoned theatre. The dilapidated theatre needed a lot of renovation. With such a historic monument they were meticulous about keeping the ceilings and the treasures they found in storage including old movie posters. Choose from High ABV IPAs and Stouts or keep it mellow with an easy sipping Kolsch. Find a bestie to share a beer reel with (a carousel beer flight expertly served in a movie reel). Hungry? Make sure to get the cauliflower bites and chorizo nachos to snack on. For more info, click on this Box Office Brewery link.

Duckpin Bowling in Shenandoah Valley
duckpin bowling is a fun twist on classic bowling

There are few duckpin bowling alleys left in the US so take advantage and play a game when you visit the Shenandoah Valley

Have you heard of duckpin bowling? Hailing from the northeast in Maryland, it began around 1900, but sadly there aren’t many duckpin bowling alleys left in the United States. There’s one alive and kicking in the Shenandoah Valley, though. Reopened under new management in 2018, the Shenandoah Bowling Lanes are located in the town of Mount Jackson, Virginia, not far from the Shenandoah Caverns, with both being a quick exit from I-81.

one of the few duckpin bowling alleys left in the US

Owner of Shenandoah Duckpin Bowling alley, Tina Bowman.

How is duckpin bowling different from regular bowling? Both the pins balls are smaller. Balls about the size of a softball and have no holes in them like regular bowling balls. Plus each player gets three turns instead of two.

Owner Tina Bowman purchased the bowling alley several years ago from the prior owner to revitalize the community. She encourages a no cell phone zone where people can revel in playing the game and enjoy time with family and friends. Games are just $5 per person per game.

Shenandoah Caverns

Many Boomers and families alike flock to the Shenandoah Valley – just off I-81 – to exploring the caverns there. However, after visiting Shenandoah Caverns be warned: This excursion might ruin you for future caverns. That’s because the Shenandoah Caverns are quite breathtaking.

shenandoah caverns in virginia

Breathtaking views at the Shenandoah Caverns in Virginia

If you aren’t up for long walks or hiking, don’t fret. The walk through the caverns is not that long. It’s about an hour at a slow pace, with stops along the way to admire the formations. And while you’re en route, make sure to drop a penny in the wishing well.

Bonus: Your guide will launch a spectacular light show during your tour, so get your cameras ready. Also note: No matter what time of day or year you schedule your visit, the temperature of the caverns constantly remains in the mid 50s. So bring a light jacket, just in case.

Admission is $25 per person. The caverns are open every day but Christmas. Check their website for current operating hours.

American Celebration on Parade

Where do parade floats go to retire?

museum of parade floats in shenandoah Valley

On your way from the Shenandoah Caverns, stop by this museum of parade floats

On the heels of your cavern visit, don’t leave the area without a visit to the American Celebrations on Parade, just down the street from the Caverns. Called the American Celebration on Parade, this impressive collection of floats is housed in a 40,000 square foot warehouse. Whether or not you are a parade lover, you can’t help but be impressed by the often wildly ornate floats towering over you. What is astonishing is that these floats were only designed to last the length of a parade (just a few short hours). But with perseverance and love bestowed upon them by the staff at this museum they live on in a sort of float afterlife. Plus, admission is free! This exhibit’s link is the same as the Shenandoah Caverns link.

— Headline image: Meems Bottom covered bridge in Virginia’s Shenandoah Valley.


Malika Bowling

Malika Bowling is the author of Food Lovers’ Guide to Atlanta and Food Blogging 101. She has been featured on HGTV, Playboy, Chowhound and Travelgirl and has been a contributing writer to USA Today. Malika also has served as a judge at various culinary competitions and food festivals, including The World Food Championships, where she is a certified judge. Besides food, travel is her passion and her most recent adventure is leading international culinary trips.