The Adams Morgan Fall PorchFest returns from 12:00 – 5:00 p.m., bringing more than 100 live performances to porches, patios, parks and businesses throughout Adams Morgan. This fall, the free neighborhood-wide music festival is expanding with the debut of the Adams Morgan PorchFest Market, adding local vintage, art, jewelry, and makers to an afternoon already filled with live music and neighborhood exploration.

The Boro is welcoming little ghosts and grown-up ghouls to Boro Park for the third annual Halloween at the Boo-ro on at 12:00 - 3:00 p.m. Spooky tunes, hands-on activities and plenty of treats will keep the Halloween spirit going all afternoon. Come dressed to impress for a frightfully festive celebration. The event is free. To register, click here.

It’s time to get your spook on and join for the annual Trick or Treat at The Square from 3:00 - 6:00 p.m. Enjoy free face painting, a live DJ, and the opening of the ice skating rink! Costumes and furry friends are encouraged. You will receive a FREE Trick or Treat at The Square bag to hold all your treats from participating businesses and vendors while supplies last. For more information, click here.

Matt & Tony’s transforms into a one-night-only Spooking Speakeasy, inviting guests to unlock an evening of Halloween cocktails, costumes, giveaways and plenty of mischief. Beginning at 5:00 p.m., those who arrive with the secret password, or book using the exclusive reservation code, will gain access to the Halloween pop-up, with the bar staying open an extra hour until 10:00 p.m. for the occasion. Those who arrive in costume will receive a complimentary spooky Jell-O shot, while the bar gets a wicked makeover with Halloween-inspired cocktails and theatrical presentations, including the Type-O-Negative Blood Bag Cocktail. The evening will also feature haunting bar snacks, a special three-course Halloween tasting menu and a selection of Matt & Tony’s favorites for those looking to stick with the classics. Available via OpenTable.

Fairmont Washington, D.C., invites you to stop by with their canine companions for their 15th annual Howl-O-Ween in the Courtyard Bar from 6:00-  7:30pm. Prizes, awarded for best-costumed doggies with their people, including overnight stays, dinners and more. Local celebrity judges will award prizes for most creative, most adorable, funniest and honorable mentions. All dogs are treated to pawsome peanut butter doggie biscuits created by Fairmont’s pastry team; canine coolers are placed throughout the courtyard too. Humans can purchase spooky Halloween-themed cocktails and Puptails for four-legged guests. There is no charge to attend Fairmont’s 15th Annual Howl-O-Ween.  To sign up, visit Howl-O-Ween Registration.

The First Ever Capitol Hill PorchFest is taking place from 2:00 - 6:00 p.m.! Join fellow Hill residents and Washingtonians for an afternoon of local music set to the beautiful backdrop of our historic neighborhood. For more information, click here.

The Fall Wine Festival & Sunset Tour will be taking place every evening from 6:00 - 9:00 p.m. You can enjoy unlimited samples, a commemorative wine glass, and after hours access to tour the mansion. For more information and to purchase a ticket, click here!

L’Auberge Chez François celebrates Virginia Wine Month with a Fabulous Fall Virginia Wine Festival & Luncheon at 11:30 a.m. You can sample nine wines from award-winning Virginia wineries during a walk-around tasting, accompanied by seasonal canapés from Chef Jacques Haeringer. Featured selections include wines from Michael Shaps, Veritas, Chrysalis, Glen Manor, Stinson, Barboursville, Early Mountain & more. The tasting runs from 11:30 a.m. to 1 p.m., followed by a four-course seasonal luncheon paired with a glass of Virginia wine. Tickets are $120 per person. Click HERE to grab your spot.

Fairfax City will celebrate the 50th Annual Fall Festival  from 10:00 a.m. to 5:00 p.m. in Old Town Fairfax. The free event will feature hundreds of artisans, live music and entertainment, food, family activities, beer gardens, and special events. Highlights include Taylor Swift tribute Cruel Summer, Sparky’s Harvest Bash, Fall for the Book’s “Meet an Author Day,” and more. Free parking and shuttle service will also be available. For additional information, including the complete entertainment schedule, vendors, activities, parking information, and festival map, click HERE.

Village at Leesburg will host its annual Monster Mash from 1:00 - 5:00 p.m., bringing a spooky afternoon of Halloween fun to the plaza. This free, family-friendly event will feature professional pumpkin carving, trick-or-treating, cookie decorating, face painting, kids and pet costume contests, and more. A Halloween Costume Contest will take place on the Main Stage from 3:30 to 4:30 p.m., with categories for kids 14 and under, families and groups, and pets. Well-mannered pets on leashes are welcome and encouraged to dress up for the occasion. Loudoun County Safety Day will also take place during the event, with the Loudoun County Sheriff’s Office sharing trick-or-treating safety tips, public safety displays, and important child safety information. Click HERE for more information.