Join Cork Wine Bar and Warren Leonard, National Sales Director of Weygandt-Metler Importing, from 2:00 - 5:00 p.m. at Cork Cleveland Park. They will help you taste and order holiday wines, explore Weygandt by the glass, and you will taste a Weygandt flight.

Join Cork Wine Bar & Market at their 14th Street location for an evening of delicious food, thoughtfully paired wines, interesting conversations. 16 seats only! 

Boxwood Winery is teaming up with award-winning Red Truck Bakery for a festive afternoon of wine and pie pairings from noon - 2:00 p.m. The event will feature four holiday-inspired sweet and savory creations from Red Truck Bakery, each thoughtfully paired with one of Boxwood’s award-winning wines. You will discover how the perfect wine pairing can enhance flavors and elevate the dining experience. Tickets are $65 per person, plus applicable taxes, fees and gratuities. Reservations can be made at www.cellarpass.com/events/easy-as-pie-wine-pairing-12545.

Join Maxwell Park and find every wine pairing you will need this Thanksgiving at their Thanksgiving walk-around wine tasting! They are pouring 25 perfectly paired wines for Thanksgiving! To purchase a ticket, click here.

Friendship Heights’ largest event — the Holiday Makers Market — returns with more than 40 makers and artisans, music, food and tastings along two blocks of Wisconsin Avenue sidewalks, from Jenifer Street to Garrison Street. View the full lineup of vendors, curated by Trishtan Foods.During the market, photographer and curator Pat Graham will host a Turnstile print pickup, photography sale and large-scale projection at the Pavilion Pop-Up Gallery, just across the street from the market.

Boxwood Estate Winery is making Christmas in Middleburg even more magical on Saturday, December 5th, with a special holiday package combining convenient parade parking and transportation, festive activities and a three-course Italian wine dinner at the winery.Guests can park at Boxwood and take complimentary shuttles to Middleburg's popular Christmas parades and festivities from 11:00 a.m. to 2:00 p.m. A coffee and hot cocoa bar adds to the holiday cheer. Return shuttles operate from 4:00 to 5:00 p.m., when guests can take photos on Boxwood's holiday float before enjoying a festive family-style dinner at their own private table between 5:00 and 7:00 p.m.The Italian holiday dinner features three courses accompanied by a glass of premium Boxwood Estate wine, with a choice of sparkling, white, rosé or red. A special children’s menu makes the celebration ideal for the entire family.The complete holiday package, including parking, shuttles, festivities and dinner, costs $140.00 per adult, plus fees, tax and an automatic 18% gratuity. Children’s tickets (ages 14 and under) are $29.00, plus fees, tax and an automatic 15% gratuity.Seating is limited, and the event typically sells out early. Reservations are required. To reserve spots, click here.  

Celebrity chef/talk-show host Carla Hall and former Washington Post food critic Tom Sietsema return to Hill Center at 7:00 p.m. for a conversation and they both have so much news to share! Carla has been touring the country with her new cookbook, “Carla Bakes: Sweet, Savory and From the Heart” (4 Color Books) and Tom is now the food correspondent for The Washington Sun. This time, Tom will interview Carla — turnabout from “Ask Tom (Almost) Anything” — and guests who saw them last year know their exchange will be lively and personal.The D.C./regional chapter of Les Dames d’Escoffier, of which Carla has been a longtime member, will host a pre-event meet-and-greet at Hill Center with Carla and Tom at 5:30 p.m., featuring savory and sweet treats from “Carla Bakes.” East City Bookshop will be onsite to sell the cookbook and Carla will happily sign books.Tickets range in price from $15.00 – $35.00. For more information, or to reserve a spot, click here. 

The Swedish Women’s Educational Association DC Chapter (SWEA DC), in collaboration with the Embassy of Sweden, will host its annual Swedish Holiday Market on Saturday, December 5, 2026, from 10:00 a.m. to 5:00 p.m. at the House of Sweden in Georgetown. Guests can experience the magic of a traditional Nordic holiday celebration featuring Scandinavian arts and crafts, Swedish glassware, books, festive treats, and live performances by Washington Spelmanslag. VIP admission is available from 10:00 a.m. to 12:00 p.m. for $20 and includes complimentary fika and/or mulled cider, along with raffle opportunities. General admission is $15 from 12:00 to 4:00 p.m., with complimentary fika included. Children ages 12 and under receive free admission. The festivities will conclude with a traditional Swedish Saint Lucia Choir Procession at 5:00 p.m. on the steps of the House of Sweden, a free performance open to the public. Advance ticket purchases are encouraged, as admission is limited and all market attendees must exit the building by 4:45 p.m. Click HERE to grab your tickets.

Enjoy a two-hour walk-around tasting featuring 30 standout wines from across the country, including California, Washington, Oregon, New York, and Virginia. The experience includes bites from The Roost, expert pours across six tasting stations, and an exclusive bottle sale with discounted prices on all featured wines. Tasting sessions from 12:00 - 2:00 p.m. and 3:00 - 5:00 p.m.

Join CityRidge DC from 4:00 - 8:00 p.m. for their 5th Annual Christmas Tree Lighting! Expect an evening of holiday activities, festive treats, train rides, crafts, and photos with Santa. There will also be a performance by The Children’s Chorus of Washington.