Join Cordelia Fishbar at 6:30 p.m. for an All Hallows' Eve Wine Dinner. Chef Josh Hunt cooks five fall courses over charcoal, while Beverage Director Miles Hunter pours "ghastly and ghoulish" bottles from the cellar. $130 per person for five courses with wine pairings, plus tax and gratuity. Tickets via Tock!

Get ready for an immersive tasting journey from the coastal breezes of the Casablanca Valley to the high-altitude vineyards tucked against the Andes. Thanks to their partnership with ProChile, they are hosting 10 exceptional Chilean producers who represent some of the best of South American winemaking. Whether you are a longtime fan of bold Carménère and crisp Sauvignon Blanc or eager to explore innovative small-batch vintages, you'll have the opportunity to sip, chat with the makers, and discover the deep roots and vibrant future of Chilean wine. Spaces for this exclusive afternoon tasting are limited, so reserve your glass today! Only $25 per guest.

Join Hank’s Oyster Bar at their Old Town Alexandria location from 11:00 a.m. - 1:00 p.m. for their 17th annual OYSTERfest. Tickets include all you can eat oysters, fried oysters, grilled chicken skewers, and much more. Their bar team will also be serving up all you can drink drinks. Tickets cost $100 per person!

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!