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Despite certain coffee shops launching pumpkin spice lattes in August, October is the month that really ushers in fall weather. It’s time to pull out your plaid shirts and warm hoodies before heading out to enjoy the changing season with family and friends.
October is a peak time for festivals before the start of the winter 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. Here’s what’s happening in and around DC, Maryland, Virginia, and West Virginia this month.
Photo courtesy of Messick’s Farm Market
Fall Pumpkin and Harvest Festivals
We love local pumpkin patches and harvest festivals so much, we did a whole post just about those! Take a look at Top Pumpkin Patches A Short Drive Away updated for 2025.
81st Annual Waterford Fair | October 3-5
National Historic Landmark of Waterford, VA
Come shop, play, tour, and make memories during this annual 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. Click here to see the fair map.
Art on the Avenue in Del Ray | October 4, 10 AM-6 PM
Mount Vernon Avenue, Alexandria, VA
Jen Walker Team of Corcoran McEnearney 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
Taste of Bethesda | October 4, 11 AM-4 PM
Norfolk Avenue in Woodmont Triangle, Bethesda, MD
The 33rd annual Taste of Bethesda will feature Bethesda’s best restaurants, four stages of live entertainment, activities for kids, and more!
Free Admission. Taste tickets 4/$5
Fall Food Festival | October 4, 11 AM-6 PM
142 N Queen Street, Martinsburg, WV
The Fall Food Festival is a vibrant celebration of Appalachian flavors and community spirit, set against the charming backdrop of downtown Martinsburg. With the rich sounds of folk music filling the air, guests can savor the season’s tastes from various food trucks, local eateries, and craft vendors. Enjoy live performances from talented musicians, a bustling beer garden, and a family-friendly atmosphere.
Harpers Ferry Highland Games | October 4 & 5
Sam Michael’s Park, Harpers Ferry, WV
Highland Games are a centuries-old tradition featuring feats of strength and skill. This year, the Harpers Ferry Celtic Culture Society is hosting two full days of Celtic athleticism, music, dance, and family fun to the Eastern Panhandle. Visitors can also explore food vendors, local artisans, and interactive cultural exhibits.
Tickets $15 in advance | $20 at the gate | Free for children under 12
Photo courtesy of Main Street Takoma
Takoma Park Street Festival | October 5, 10 AM-5 PM
Carroll Avenue, Takoma Park, MD
This popular festival returns for its 44th year of music, vendors, food, and fun in Takoma Park. Explore over 185 vendor booths, live music from 18 local bands, food trucks, and more. Takoma’s unique shops, restaurants, and cafes are all open and welcoming visitors. Event is rain or shine.
Free Admission
Festival of Leaves | October 10 & 11
Downtown, Front Royal, VA
Don’t miss 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.
$5 Cover Charge
Mount Vernon Fall Wine Festival & Sunset Tour | October 10-12
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
Capital Art & Craft Festival | October 10-12
Dulles Expo Center, Chantilly, VA
This three-day event features 250+ artists and their unique handmade treasures that are perfect for any home or holiday gift giving.
The Virginia Fall Races | October 11
Glenwood Park, Middleburg, VA
Immerse yourself in history at Glenwood Park, the oldest continuous race course in Virginia. Corcoran McEnearney is excited to join 10,000 enthusiastic fans to witness thundering hooves and heart-pounding steeplechase action. A tradition unlike any other!
Photo courtesy of Falls Church Farm Day
Falls Church Farm Day | October 11, 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
49th Annual Fairfax Fall Festival | October 11, 10 AM-5 PM
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.
Free Admission
Snallygaster Beer Festival | October 11
Pennsylvania Ave NW between 3rd & 7th, Washington, DC
Those in the know know: Snallygaster is the District’s biggest & beastliest beer festival, bar none. Festival goers can expect a mind-boggling selection of no fewer than 450 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.
Paws in the Park | October 12, 11 AM-4 PM
Oronoco Bay Park, Alexandria, VA
Paws in the Park is a FREE, fun-filled day for the whole family (including pets) that benefits the Animal Welfare League of Alexandria. Live entertainment, music, food and drink, vendors, shopping, and adorable adoptable animals! Our Alexandria Office and Bobby Mahoney are proud to sponsor this year’s costume contest!
Free Admission
DC Wine Fest | October 18
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.
Walk to Bust Cancer | October 19, 7:30 AM
Fort Hunt Park, Alexandria, VA
The Breast Center Foundation marks 10 years of providing access to life-saving screenings for women in Northern Virginia. Join the Corcoran McEnearney team for this inspiring event or donate here.
Photo courtesy of Virginia Gold Cup Races
International Gold Cup | October 25
Tailgating at the Virginia Gold Cup races is a time-honored tradition, so make the most of the day and participate in the Tailgate Contest. The best tailgates have a theme, decorations, and special food and drink recipes. Race Day just wouldn’t be the same without the fabulous Hat Contest—and this year promises to be bigger, bolder, and more outrageous than ever!
Del Ray Halloween Parade | October 26, 2 PM
Del Ray, Alexandria, VA
The parade begins at Mt. Vernon Avenue south of E. Bellefonte. Children, pets, and decorated strollers are invited to march and show off their costumes! This parade ends with live music and an award presentation at the Mount Vernon Rec Center field. Jen Walker Team of Corcoran McEnearney is proud to sponsor the Best Decorated House & Business Contests.
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 with spectacular views of the Washington, DC, skyline as a backdrop.
Visit corcoranmce.com to search listings for sale in Washington, D.C., Maryland, Virginia, and West Virginia.
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