5 Wonderfully Full Days of History in and Around Shepherdstown, WV

Exterior of the inn after spring rain with purple iris and white dogwood in bloom.Hi, I’m the innkeeper of the Thomas Shepherd Inn in Shepherdstown, WV, West Virginia’s oldest town. Find us in West Virginia’s Eastern Panhandle, steeped in history from Colonial times to the present.  Minutes from Harpers Ferry and Antietam National Battlefield, Shepherdstown has great accommodations, wonderful restaurants and shops and makes a great base camp for exploring the history of the town and the surrounding area.

I’ll let you in on a little secret.  Innkeepers don’t get out much!  So, sometimes it’s fun to think about what I would do if I was my guest.  How would I plan, what would I see and do if I was coming to my inn to experience the history of West Virginia’s Eastern Panhandle?  So indulge me in my fantasy trip to my own inn in Shepherdstown.  This is how I would proceed.

When to Come:  Any time but April through October will offer the best weather and nice daytime temperatures.

What to Bring:  Comfortable clothes and shoes to walk in (lots of walking!), sunscreen and a water bottle.  A small day-pack will also come in handy.

Before You Come:

Make sure “Clio – The History App” is installed on your phone.  Clio gives you the scoop on everything historic with vetted and often referenced articles.  Clio uses your location to access articles, pictures, maps and directions to all things historic.  Constantly growing and improving, Clio currently has 383 articles of interest within a 50 mile radius of Shepherdstown.  Free for both Android and iPhone.  You won’t know how you ever got by without it.

Visit the Shepherdstown Visitors Center.  Visit online, or call  them at 304-876-2786 and stop in when you arrive in town at 201 South Princess Street.  The Visitors Center is open from 10 am – 4 pm daily and staffed with knowledgeable volunteers who can answer your questions, give you great ideas, fill you in on the latest happenings in Shepherdstown and, quite honestly, make you never want to leave!

This is my fantasy trip so I’m staying at the Thomas Shepherd Inn.  I hear the innkeepers make a great breakfast and do all they can to make their guests really happy.  If they happen to be full there are several other good lodging options in town to meet your travel needs.  Visit Shepherdstown.info/stay/ for more information.

Day 1 – Tuesday

I can’t wait to get started so, of course, I arrive in Shepherdstown well before check-in.  Pretty much all of Shepherdstown in the historic district so Clio will have information about most of the buildings in town.

But first, I need a really good cup of coffee!  The folks at Lost Dog Coffee are very serious about providing a quality experience when it comes to coffee or tea and their decor, very 60’s, will help you ease your way into the past.

A quick stop at the Visitors Center answers my last minute questions.  The current Visitors Center building was originally built in 1848 by the State of Virginia, when West Virginia was still part of Virginia, and is believed to be the oldest free school house in West Virginia.

Lunch at the Blue Moon Cafe on Princess Street.  A converted 1920’s service station with a real college town feel, they use great ingredients to make some of the best salads, sandwiches and wraps around.  If the weather is warm, ask about their outdoor seating.  It’s an experience in itself under shaded trees with the Town Run stream flowing by.

Check-in to the Thomas Shepherd Inn and get settled.  Perhaps a nice cup of tea and a home baked cookie on the upstairs porch.

Explore downtown Shepherdstown.  The Visitors Center has a walking tour pamphlet or use Clio to discover the history of the town’s historic buildings, some from as early as the 1790s.  The Mecklenburg Inn occupies a building built in 1795.  You can enjoy a local brew any day in their garden.

Dinner at Bistro 112.  French and delicious!

Day 2 – Wednesday

Monument to Pennsylvania Infantry at Antietam National Battlefield in winter with leafless trees and bright blue, cloudless sky.I’m visiting Antietam National Battlefield today, the site of the bloodiest single day’s battle in American history.  There are many ways to visit Antietam but I’m looking for an in-depth view of the battle and the times so I’ll be taking a private tour. 

Antietam Battlefield Guides undergo rigorous training and mentoring to be able to speak to the times as well as the battle.  Tours are 2-8 hours in length depending on your needs and if you want to see other battle sites (South Mountain and/or Harpers Ferry).  Make a reservation by calling 301-432-4329.  Visitors provide transportation for the guide.

If you want to be able to look and not drive then RCM History Tours is a great choice.  Again, tours are 2-8 hours and you can build your own tour if you wish.  Transportation is provided for up to 4 people.  Call 301-491-0002 for reservations or email rcmhistorytours@gmail.com.

Lunch will depend on where I am in my tour.  If I’m in Sharpsburg I’ll give Captain Bender’s Tavern a try.  They have been serving the area for over 30 years.  After lunch, a stop at Nutter’s Ice Cream.  Servings are large and there is often a line.  It’s worth the wait.

Return to Shepherdstown.

I’ll stop in at Four Season’s Books to browse their marvelously curated selection of local and Civil War history books.  One of my favorites is “Liar, Temptress, Soldier, Spy” by Karen Abbott.  It chronicles the lives of 4 women and their roles in the Civil War.  One of the four is Martinsburg’s own Belle Boyd.

Dinner at the Press Room.  Always a good idea to have a reservation here.

After dinner I’m taking the  Shepherdstown Mystery Walk.  West Virginia’s oldest and most haunted town has plenty of history, legends, ghosts and an elephant!  It’s a 90 minute walk into the past.  Call 301-639-0351 for reservations.

Day 3 – Thursday

View of Shenandoah River and bridge from Jefferson Rock. Summer foliage with red and orange streaked sunrise.I’m spending the day at Harpers Ferry National Historical Park.  It’s always a good idea to park at the Park Visitor Center and take the free shuttle bus into town.  Buses run every 15 minutes and stop at several locations in the park.

Over 20 museums are located in Harpers Ferry historic downtown and highlight John Brown’s Raid, Civil War times and the Lewis and Clark expedition.  Climb the steps to Jefferson Rock for a breath taking view of the confluence of the Potomac and Shenandoah Rivers.

Visit True Treats Candy store.  A one-of-a-kind store, True Treats has researched the history of candy from earliest times to the mid 1900s and displays them in chronological  order.  Truly a treat!

Use Clio here for their Harpers Ferry Lower Town tour or their African American History tour of Harpers Ferry.

Return to Shepherdstown, relax a bit, and then dinner at Domestic for some delicious regional cuisine.

Thursday means it’s Old Time Jam Session night at O’Hurley’s General Store.  Over 35 years of great music every Thursday night.  The music is Appalachian/Celtic, the instruments authentic, the musicians talented and the experience is unforgettable!  They start at about 7:30 pm and play until they are tired.

Day 4- Friday

Rumsey Monument- stone pedestal with globe on topI’ll take a morning walk in town to visit the Rumsey Monument and then to the Old Episcopal Graveyard on North Church Street.  Graves date from before the Revolutionary War. Then over to the Shepherd Cemetery on New Street to get a feel for the family that settled the town.

Go to the Community Garden Market to pick up sandwiches, snacks and drinks for a picnic.  Made to order sandwiches (named after Civil War Generals) and salads that are good and good for you.

On the way to the park stop at Elmwood Cemetery, about 1/2 mile from town on Rt. 480.  There are over 100 Confederate soldiers buried here.  Pamphlets are available to show the way.

Continue on Rt. 480 to Morgans Grove Park, the start of the Revolutionary War Bee Line March.  Clio will tell you more.  Enjoy your picnic lunch and explore the stone spring house, the source of the Town Run that flows through Shepherdstown to the Potomac.

Visit Charles Town, named after George Washington’s brother Charles.  Take the Clio walking tour of Charles Town and visit the Jefferson County Museum and the Jefferson County Court House the site of John Brown’s treason trial.

Return to Shepherdstown

Dinner at the Bavarian Inn.  Always a great meal, I like the cozy feel of the Rathskeller or perhaps their new brew pub.

Day 5 – Saturday

Check out from the inn at 11 am.

Walk down to the Entler Hotel and Museum at 129 East German Street.  Get a feel for small town life in the Civil War era and see the half scale model of James Rumsey’s steam boat.

Lunch at Maria’s Taqueria for the best fish tacos ever.

Stop at the Belle Boyd House and Berkeley County Museum in Martinsburg.  It highlights the life of Belle Boyd and offers a glimpse into Civil War life.

Continue on your journey home knowing that you have only scratched the surface of the history that Shepherdstown and its surrounding area has to offer.


1 thought on “5 Wonderfully Full Days of History in and Around Shepherdstown, WV

  1. This is so cool. This town was named after my direct family. Im hoping to come there one of these days and get in touch with my roots. My direct lineage ancestor was Thomas shepherds brother john.

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