Downtowns and historic places are filled with fall festivals, Christmas celebrations and winter warmth
JEFFERSON COUNTY & BERKELEY COUNTY, WEST VIRGINIA–OCTOBER 2025–An escape to West Virginia’s Eastern Panhandle is refreshing any time of year, but as fall turns to winter, the region’s warm, welcoming character shines as bright as its holiday lights.
Historic downtowns offer idyllic settings
Jefferson County and Berkeley County are just over an hour’s drive northwest of Washington, D.C. Located between Interstates 81 and 70, this respite from the city is easily accessible by car via U.S. 340 and West Virginian Route 9 or by rail from Washington or Baltimore. This is the perfect destination for a fall or winter escape from the city and visitors find a variety of ways to enjoy it. From quiet, cozy days to brisk outdoor adventures to downtown celebrations, there are plenty of ways to enjoy a seasonal respite.
Cool, crisp air and vibrant colors draw many to explore the variety of the region’s outdoor attractions. From exploring the streets of Harpers Ferry National Historic Park (171 Shoreline Drive, Harpers Ferry, West Virginia 25425; 304-535-6029) to cycling the historic Chesapeake & Ohio Canal towpath or hiking the trails of the 22,000-acre Sleepy Creek Wildlife Management Area (Berkeley Springs, West Virginia 25411; 304-822-3551) or the famed Appalachian Trail, which crosses over the Potomac River into West Virginia, the mountain air and exceptional views are inviting.
The downtown streetscapes are inviting here and offer a welcoming mix of old and new. Inside the historic buildings that line the streets is an eclectic collection of locally owned businesses. Cozy cafes and coffee shops like Sibling Coffee Roasters (109 West Washington Street, Charles Town, West Virginia 25414; 304-885-8492), the Daily Grind (778 Foxcroft Avenue, Martinsburg, West Virginia 25401; 304-262-9722) and German Street Marketplace Coffee & Candlery (103 West German Street, Shepherdstown, West Virginia 25443; 304-876-1106). Each offers specialty coffees, friendly service and a relaxing atmosphere which combine to make everyone feel at home.
A self-proclaimed haven for bibliophiles, Four Seasons Books (114 West German Street. Shepherdstown, West Virginia 25443; 304-876-3486) is a beloved local independent book store that offers a unique selection of new, used and discount books. Creative Procrastinations And Whimsical Necessities (132 East German Street, Shepherdstown, West Virginia 25443; 410-917-7262) is an emporium offering art, toys, stationery, gifts, but specializes in “fairies and fun.” Unique treats can be found at True Treats Historic Candy (144 High Street, Harpers Ferry, West Virginia 25425; 304-461-4714), the nation’s only research-based candy store. Patrons will find more than 500 historic teas, candies and confections here, including “retro bites and penny delights.” Defluri’s Fine Chocolates (130 North Queen Street, Martinsburg, West Virginia 25401; 304-264-3698) is a family-owned chocolatier known for handcrafting a collection of luscious sweets including sea salt caramels, artisanal dark chocolate thin mints and cream-centered chocolates.
Fall fun and spooky tours
Hayrides, corn mazes and pumpkin patches are fall traditions here and no place does them better than Orr’s Farm Market (682 Orr Drive, Martinsburg, West Virginia 25403; 304-263-1168) The market is year-round but fall is special here, when the pumpkin patch and apple-picking are in full swing. The selection of homemade jams and baked goods is the perfect pairing with scenic orchard views. Downtown markets are popular on fall weekends throughout the heart of the Eastern Panhandle. The historic Martinsburg Roundhouse (100 East Liberty Street, Martinsburg, West Virginia 25404; 304-260-4141) – the sole surviving roundhouse of its kind in the world – is the setting for the Roundhouse Farmers Market on fall Saturdays. Soaps, baked goods, pottery and lemonade are just some of the homemade specialties to be found. Charles Town Farmers Market (100 South Samuel Street, Charles Town, West Virginia 25414) is also held on Saturdays through October. Farmers, bakers, artists and musicians are all on hand to share their bounty. The Shepherdstown Farmers Market (South King Street, Shepherdstown, West Virginia 25443) has a 30-year history and brings a wealth of local produce, products and crafts each Sunday morning through December.
In Martinsburg, September’s Fall Arts Fest at Blue Goose Pottery (7278 Hedgesville Road, Hedgesville, West Virginia 25427; 304-279-9075) is the perfect outdoor event to kick off fall and features the work of more than a dozen West Virginia artisans. The Fall Food Fest (204 South Queen Street, Martinsburg, West Virginia, 25401; 304-262-4200) features food trucks with Appalachian inspired dishes, unique regional vendors and live music.
For three days in September, the Mountain Heritage Arts and Crafts Festival (1707 Old Leetown Pike, Kearneysville, West Virginia 25430) celebrates the best of this diverse region’s artisans. More than 160 artists and crafters display their work and visitors can also enjoy the performances of bluegrass musicians and the creations of regional vintners and craft brewers.
Boo Fest is Shepherdstown’s way of celebrating all things spooky and supernatural during October. German Street is decked out with festive decorations, restaurants and pubs offer fun seasonal specials and events are held by local organizations. The third weekend in October (16th-19th) brings the Mountain State Apple Harvest Festival (Berkeley County Youth Fairgrounds, 2419 Golf Course Road, Martinsburg, West Virginia 25405) which celebrates the apple industry with four days of fun. The festival is designed to honor special traditions of the past and create memorable moments for today’s families. There are competitions for apple peeling, eating and pie baking, as well as a parade and even a rodeo.
The second week of November, November 8-9, 2025, artists welcome visitors into their realm during the Over The Mountain Studio Tour. Approximately a dozen studios are part of the self-guided tour that crosses beautiful rolling hills between sprawling farms, studio spaces and charming historic homes.
This is also the perfect time of year for those who love haunted walks and ghost tours. The area is part of the West Virginia Paranormal Trail and its history is rife with eerie stories that bring chills to the spine. Charles Town Ghost Tours (681-296-2989) and Small Town Ghost Tours (117 East German Street, Shepherdstown, West Virginia 25443; 301-991-0265) take visitors through the streets and into the stories of the haunts, haints and paranormal activities here. Charles Town, Sharpsburg, Shepherdstown and Harpers Ferry all have tantalizing tales to tell.
Celebrating Christmas
The Christmas season is a magical experience. Here, a vibrant community spirit is on display as historic sites and preserved downtowns come alive with lights, parades and holiday celebrations as the Christmas season gets into full swing.
Christmas in Shepherdstown (German Street, Shepherdstown, West Virginia 25443) kicks off the season on the day after Thanksgiving and the celebrations continue through December. The annual return of Santa Claus is the main event as the celebration lights up the town and hosts an open house for all. Businesses don festive decorations and stay open late, Mrs. Claus reads stories and, while chestnuts are roasting and music is playing, the Grinch, Cindy Lou and her Who friends prepare for Santa Claus’s arrival.
The cities of Charles Town and Ranson light up for the holidays as Christmas in Charles Town (101 East Washington Street, Charles Town, West Virginia 25414; 304-725-2311) kicks off each year. Homes and businesses decorate and shine brightly as Merry and Bright City Lights invites all to celebrate. A parade through the streets also highlights the season and limited-edition holiday ornaments are precious keepsakes each year.
Main Street Martinsburg (Event location: 100 East King Street, Martinsburg, West Virginia, 25401; 304-262-4200) celebrations begin on December 6th with the Christmas Tree Lighting, a traditional family favorite event, filled with live music and cheer leading up to the magical moment when the tree shines brightly. Also on December 6th, Christmas on Main is a festive day of Christmas fun. Live music, food trucks with delicious eats, the Naughty & Nice Bar and free children’s activities are all a part of this special event. A Christmas Market and downtown holiday shopping make finding that special gift a joy. Each year’s Christmas Parade on December 9th adds to the downtown holiday fun as the streets come alive and Santa makes an appearance.
Colonial Christmas at the General Adam Stephen House (309 East John Street, Martinsburg, West Virginia, 25401; 304) 267-4434) is another special tradition in Martinsburg. Each year, skits, entertainment, a bonfire and refreshments thrill guests. This historic landmark was built of native limestone in the late 1770s by town founder and Revolutionary War general Adam Stephen. This year’s event dates are December 6th, 7th, 13th and 14th.
There’s nothing quite like celebrating the season at Harpers Ferry National Historic Park (171 Shoreline Drive, Harpers Ferry, West Virginia 25425; 304-535-6029). This is the idyllic setting for Olde Tyme Christmas. For two weekends in December, wagon rides, a tree lighting, ornament making, live nativity, a yule log fire and caroling bring a traditional Christmas celebration to life in this unique setting. Visitors can also enjoy historic tours, a Handmade Holiday Market and extended shopping hours.
Winter respite
There’s no place better to relax and recharge for the new year, whether the choice is enjoying the views of the snow-covered landscape or getting out and enjoying winter walks on the many scenic trails. To add excitement to any winter visit, Snow Riders (408 Alstadts Hill Road, Harpers Ferry, West Virginia 25425; 304-535-2665) offers snow tubing on 12 lanes down the longest tubing slope on the East Coast. There are even multi-color LED disco light shows to tube by at night. Each January, Frosty Fest offers a weekend of winter fun that ranges from crafting and cooking classes to concerts, mystery walks and even snowman building events.
Where to stay
A wide range of lodging options are available throughout Jefferson and Berkeley counties, including a full list of familiar national and regional hotel brands. There are also options for those looking for unique lodging options. Here are just a few examples:
Apple B&B and Gallery (129 West Burke Street, Martinsburg, West Virginia 25401; 304-901-5454) is a bed and breakfast with an artistic flair. Located in a beautifully restored 1800s Greek Revival home, the Apple is in the heart of downtown Martinsburg, close to shopping, dining and attractions.
Bavarian Inn (164 Shepherd Grade Road, Shepherdstown, West Virginia 25443; 304-876-2551) has welcomed visitors to Shepherdstown for more than 45 years. Perched on a bluff above the Potomac River, the European-inspired resort includes an onsite restaurant and brew pub.
The Meadow Cottages at The Woods (1630 The Woods Road, Hedgesville, West Virginia 25427; 304-754-7977) offers tranquility and beauty amid 1,800 acres at the northern gateway to the Shenandoah Valley and is also a favorite for those who want to enjoy a day of golf or a spa experience.
Rockhaven B & B (900 Fillmore Street, Harpers Ferry, West Virginia 25425; 304-535-8235) is the perfect place for a tranquil getaway in a quiet neighborhood with the Harpers Ferry historic district. The welcoming home offers two spacious, contemporary guest suites.
Hampton Inn & Suites Charles Town (157 Pimlico Drive, Charles Town, West Virginia 25414; 304-725-2200) is located just across the street from Hollywood Casino at Charles Town Races and offers a host of amenities in a convenient setting.