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Despite certain coffee shops launching pumpkin spice lattes in August, October is the month that really ushers in fall weather and events. It’s time to pull out your plaid shirts and warm hoodies before heading out to enjoy the changing season with family and friends. Check out what is happening in and around DC, Maryland, Virginia, and West Virginia this month.
FESTIVALS, FOOD & FUN
October is a peak time for festivals before the start of the holiday season. Harvest themes abound with events focusing on beer, wine, apples, and pumpkins! It’s also a popular month for equestrian events in Virginia’s Countryside.
Photo courtesy of Fall Pumpkin Harvest Festival
Fall Pumpkin Harvest Festival | Through October 31
Great Country Farms, Bluemont, VA
Come celebrate Fall Y’all and enjoy an unforgettable experience picking pumpkins, getting lost in their corn maze, and roasting marshmallows at the bonfire. Don’t forget those freshly made cider donuts!
Pumpkin Spice and Everything Nice 1M, 5K, 10K, 13.1 26.2 Virtual Race | Through October 31
Washington, DC
Did you know that October 1 is National Pumpkin Spice Day? Celebrate with this first ever Pumpkin Spice and Everything Nice 1M, 5K, 10K, 13.1 26.2 virtual race!
October is also Pregnancy & Infant Loss Awareness Month. You have the entire month of October 2024 to complete the race. A percentage of your race registration fees will be donated to the Stillborn And Infant Loss Support (SAILS), supporting their critical work helping those who have lost their child. They are not alone.
Leesburg First Friday | October 4
McEnearney Associates & Downtown Historic Leesburg, VA
Stroll through Historic Downtown Leesburg on the first Friday of each month and visit shops, restaurants, art galleries, and offices to enjoy live music, art exhibits, wine tastings, book signings, shopping, and dining at local small businesses. Free & fun!
Stop by our McEnearney Associates | Middleburg Real Estate | Atoka Properties office on Market Street, and join us for an art display by Lydia Marie Elizabeth, live music, food & drinks!
Fall Festival LHGC | October 4, 5-8 PM
Locust Hill Golf Course, Charles Town, WV
Enjoy fun and activities with friends and family at the Locust Hill Golf Course in Charles Town. There will be a moon bounce, live music by Brad the Guitar Guy, tap takeover, food and drink specials, and lastly a fire pit with s’mores.
Waterford Fair | October 4-6
National Historic Landmark of Waterford, VA
Come shop, play, tour, and make memories during this 79 year old tradition. The fair is the mid-Atlantic’s quintessential fall festival with demonstrations by fine heritage & contemporary craft artisans, living historians, a juried art show, historic properties tour, local libations, and entertainment for all ages.
Photo courtesy of Mount Vernon
Mount Vernon Fall Wine Festival & Sunset Tour | October 4-6
Mount Vernon Estate, Mt Vernon, VA
Bring a blanket and sample wines from 20 different Virginia wineries on the East Lawn of George Washington’s beautiful estate overlooking the Potomac River. Food will be available for purchase.
Member Tickets | Non-Member Tickets
Falls Church Farm Day | October 5, 10 AM-3 PM
Cherry Hill Park, Falls Church, VA
Enjoy a day of old fashioned fun and activities for the whole family, including a petting farm, pony rides, pumpkin painting, scarecrow making (bring your own long pants and a sleeved shirt), live music, tours of the Cherry Hill Farmhouse and barn, blacksmith demonstrations, and more.
Free Admission
Art on the Avenue in Del Ray | October 5, 10 AM – 6 PM
Mount Vernon Avenue, Alexandria, VA
Jen Walker Team of McEnearney Associates is a proud sponsor of the Annual Art on the Avenue. This multicultural event includes juried artists, live music, food vendors, interactive art activities, and kids’ activities.
Free Admission
Capital Art & Craft Festival | October 11-13
Dulles Expo Center, Chantilly, VA
This three-day eventl features 250+ artists and their unique handmade treasures that are perfect for any home or holiday gift giving.
Fairfax Fall Festival | October 12
Old Town Square, Fairfax, VA
Still a hometown celebration, the Fall Festival has grown to include more than 400 arts, crafts, information, food & gourmet food vendors, children’s activities, and three stages of music and entertainment for all ages. Stay for the After Fest Concert in Old Town Square.
Free Admission
Photo courtesy of Festival of Leaves
Festival of Leaves | October 11
414 East Main Street, Front Royal, VA
We would love to invite you to Front Royal’s Ultimate Autumn Experience, the 52nd Annual Festival of Leaves. This two-day celebration begins with Dancing Downtown on Friday and continues on Saturday as one of the biggest Festivals in the Valley. As a proud sponsor of this wonderful event, we will have a stand with giveaways. Stop by!
$5 Cover Charge
Snallygaster Beer Festival | October 12
Pennsylvania Ave NW between 3rd & 6th, Washington, DC
Those in the know know: Snallygaster is the District’s biggest & beastliest beer festival, bar none. And on October 12 the merry monster makes its triumphant return to DC for its 11th year as a rollicking tribute to the wonderful world of craft beer. Festival goers can expect a mind-boggling selection of no fewer than 350 highly sought-after brews on draft from 175+ of the finest American and international producers set against a backdrop of local food trucks and two stages of live music.
The Virginia Fall Races | October 12
Glenwood Park, Middleburg, VA
Immerse yourself in history at Glenwood Park, the oldest continuous race course in Virginia. Join 10,000 enthusiastic fans to witness thundering hooves and heart-pounding steeplechase action.
We are excited to be hosting a tailgate at the Fall Races with food, drinks and great company. So please stop by and say hello!
DC Wine Fest | October 19
Dock 5 @ Union Market, Washington, DC
A wine tasting experience that aims to stimulate all your senses. All wine tastings are included in your ticket.
International Gold Cup | October 27
Glenwood Park, Middleburg, VA
This year, the International Gold Cup moves to Glenwood Park in Middleburg and will be run on Sunday. Tailgating at the races is a time-honored tradition, so make the most of the day and participate in the Tailgate Contest. Secure your tickets now, they go fast!
Photo courtesy of Visit Del Ray
Del Ray Halloween Parade | October 27
Del Ray, Alexandria, VA
The parade begins at Mt. Vernon Avenue south of E. Bellefonte and continues down to the Mt. Vernon Recreation Center fields at Mt. Vernon and Commonwealth Avenues for live music by Mars Rodeo and an awards presentation for the pet & stroller contests, plus best-decorated house and business. All are invited to march and show off their finest Halloween garb! Jen Walker Team of McEnearney Associates is a proud sponsor of this popular event.
Free Admission
Embassy Row Rooftop Halloween under the Stars | October 31
The Ven at Embassy Row, Washington, DC
Celebrate Halloween with an Embassy Row Rooftop Dance Soiree under the stars featuring two live bands performing swing and salsa music. The evening begins with swing and salsa dance lessons followed by a haunted battle of the bands as a swing and salsa band takes the stage to perform music for an unforgettable Halloween Soiree under the stars with spectacular views of the Washington, DC skyline as a backdrop.
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