Although some coffee shops launched 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 winter holiday season begins. 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.
Pumpkin Festivals and Haunted History
Fall fun is abundant this month, and we couldn’t fit all the events we are looking forward to into one post. We love local pumpkin patches and harvest festivals so much, we did a whole post just about those! Take a look at Pick of the Patch: Pumpkin Farms Near the DMV, updated for 2026. Or, if you prefer ghost stories, check out our picks at Step into Spooky Season: Haunted History Across the DMV.
WASHINGTON, DC
The Legend of Sleepy Hollow | Through October 18
Washington Stage Guild, Washington, DC
Rediscover the timeless tale of the headless horseman in this one-actor performance of Washington Irving’s spooky and cautionary tale of overconfident schoolmaster Ichabod Crane and his encounter with the terrifying ghost in search of his head.
Snallygaster Beer Festival | October 10
Pennsylvania Ave NW between 3rd & 7th, Washington, DC
For the past 14 years, the Snallygaster has been 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.
DC Wine Fest | October 16 and 17
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.
Adams Morgan Apple Festival | October 24, 10 AM-1 PM
Every fall, Adams Morgan comes alive with the sights, scents, and tastes of the season during the annual Apple Festival. This community favorite features a homemade apple pie baking contest judged by local leaders. Festival-goers can purchase pie slices to support a neighborhood nonprofit, enjoy fall-themed specials from local businesses, and take in the cozy, seasonal atmosphere.
Free Admission
Embassy Row Rooftop Halloween under the Stars | October 31, 6:30-10 PM
The Ven at Embassy Row, Washington, DC
Celebrate Halloween with Embassy Row’s Annual 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.
Photos courtesy of Corcoran McEnearney, Taste of Bethesda, and Washington Stage Guild.
MARYLAND
Annual Taste of Bethesda | October 3, 11 AM-4 PM
Norfolk Avenue in Woodmont Triangle, Bethesda, MD
The 34th 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/$10
Takoma Park Street Festival | October 4, 10 AM-5 PM
Carroll Avenue, Takoma Park, MD
This popular festival returns for its 45th 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. The event is rain or shine!
Free Admission
Annapolis Sailboat Show | October 15-18
One of the most favorite events by those who love the water is back, bringing sailboats from all around the world to floating docks for an annual celebration of sailing. Explore everything from sleek racers to spacious cruisers, then browse waterfront tents filled with nautical gear, accessories, and opportunities to learn or plan your next adventure.
60th Annual US Oyster Festival | October 17-18
St. Mary’s County Fairgrounds, Leonardtown, MD
With fun for the whole family, this is a great event to drive out to! There will be over 100 vendors and exhibitors to explore, three stages of live music, and the Chesapeake Mermaid for kids to meet. And the main attraction, the oyster cook-off showcase, starts at 11:30 AM daily!
VIRGINIA
82nd Annual Waterford Fair | October 2-4
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.
30th Annual Art on the Avenue in Del Ray | October 3, 10 AM-6 PM
Mount Vernon Avenue, Alexandria, VA
Each year, Art on the Avenue fills Mount Vernon Avenue in Alexandria’s Del Ray neighborhood with art, music, food, and family fun. Visitors can browse work from more than 300 artists, enjoy live performances, sample everything from barbecue to homemade cider, and join in kids’ activities like pumpkin painting and scarecrow stuffing.
Free Admission
Festival of Leaves | October 10th, 10 AM-6 PM
Don’t miss Front Royal’s Ultimate Autumn Experience, the 54th Annual Festival of Leaves, that goes on rain or shine. There will be more than 250 vendors, food trucks, live music, a car show, Oktoberfest Garden, and a kids zone!
Free Admission
Mount Vernon Fall Wine Festival & Sunset Tour | October 9-11, 6 PM-9 PM
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
The Virginia Fall Races | October 10, 12:30 PM
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!
Falls Church Farm Day | October 10, 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
50th Annual Fairfax Fall Festival | October 10, 10 AM-5 PM
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
Paws in the Park | October 11, 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
Lucketts Fall Market | October 16-18
890 W Main Street, Berryville, VA
Discover one-of-a-kind treasures at the Lucketts Fall Market, where more than 200 East Coast vendors showcase antique, vintage, and repurposed furnishings to give your home a little extra character. With live music, Vanish beer gardens, delicious food trucks, and hands-on workshops, this three-day event offers a festive fall weekend filled with shopping and inspiration.
Walk to Bust Cancer | October 18, 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.
Adult Walker $40 | Youth Walker $20
Inaugural Taste of Gold Cup & International Gold Cup | October 23 & 24
Join the Virginia Gold Cup Association in kicking off their races the night before at their Inaugural Taste of Gold Cup or join them in tailgating at the Virginia Gold Cup races! It is a time-honored tradition, so make the most of the day and participate in the Tailgate Contest. 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!
Inaugural Taste of Gold Cup Tickets | International Gold Cup Tickets
Del Ray Halloween Parade | October 25, 2 PM
Mount Vernon Avenue, 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 has been nominated as one of the 10 best Halloween parades in the country by USA Today!
Free Admission
WEST VIRGINIA
Fall Food Festival | October 3, 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 3 & 4
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 in 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 | Please note: only ADA-compliant service animals are permitted
