On Saturday, August 22, Whitlow's on U Street is bringing the laughs and high-octane energy of Talladega Nights to life with a Ricky Bobby-themed party celebrating the night of the Freedom 250 Grand Prix. Guests are encouraged to pull out their cut-off flannels and jorts for a night of themed fun featuring specialty cocktails like the "Shake and Bake Spicy Margarita" and the "Pit Stop Paloma." The restaurant will be decked out in Talladega Nights décor, while staff will embrace the theme in NASCAR jumpsuits, cut-off flannels, jorts, and trucker hats. Jose Cuervo representatives will be on site handing out swag and temporary tattoos, and DJs Killabeats24 and Davy Jones will keep the party going with music all night long.

Wine lovers can explore the world of skin contact wines at 50 Shades of Grapes on Sunday, August 16, from 1:00 to 3:00 p.m. at The Eastern. This guided tasting will feature four wines with varying levels of skin contact, offering guests the opportunity to discover the unique flavors, textures, and techniques behind this distinctive style. The class will be led by The Eastern's Wine Director, Eric Morris, alongside D.C.-based sommelier and Massanois wine representative Alexa Jaenicke, who will share insights from the importer’s curated portfolio of family-owned wineries. Click HERE to purchase your ticket.

At 6:00 p.m., Immigrant Food is hosting its 6th annual live Immigrant Comedy Night! The event is in collaboration with KAMA DC, showcasing a lineup of local, immigrant comedians while guests enjoy Immigrant Food's signature internationally inspired menu and drinks. Highlighted talent includes Kevin Chen, Latif Idris, Adaobi Ugochukwu, and Cynthia Via. Tickets here.

Live! Casino & Hotel Maryland is serving up special prix fixe menus during its Summer Restaurant Week, taking place August 16 –27. Available Sunday through Thursday, guests can enjoy seasonal three-course dinners at five of the resort's dining destinations: Sports & Social Maryland ($35), Truong Tien Restaurant ($35), Luk Fu ($39), David's Restaurant & Bar ($45), and The Prime Rib at Live! ($75). Executive Chef Phillip Stephenson shared that this year's event highlights the creativity of the culinary team, with a special focus on the resort's newest restaurant, Truong Tien, where guests can experience authentic Vietnamese cuisine. Whether visiting for the first time or returning for another meal, Restaurant Week offers the perfect opportunity to discover a new favorite dish to enjoy with family and friends. Click HERE for more information.

Following the success of Bolivian Fest DC, Casa Kantuta is launching the inaugural Bolivian Cultural Weekend on August 15 through 16 to celebrate Bolivia's Independence Day. The 2-day event includes the Seis de Agosto Party at Metrobar with Bolivian dance performances, cocktails, and live music, followed by El Mercadito Boliviano at Portrait Social in Georgetown, featuring local artists, authentic food, coffee, artisan vendors, and Bolivian-owned small businesses; casakantuta.com

Join The Roost for a walk-around tasting and bottle sale of 30 of their favorite wines made in South Africa! They are gathering some of the best DC wine distributors to share some of their favorite wines made in the historical yet innovative wine regions of South Africa! Join them for a walk-around tasting featuring a 30 ultra-fine wines crafted sustainably in South Africa. The price is $45 per person to taste through all of our favorite sparkling, white, rosé, and red wines, and gain access to our fabulous bottle sale! Purchase a ticket here!

Eat the City is back! Aslin Beer Company is teaming up with Rooster & Owl for a one-night-only dinner collaboration! Grab your ticket and get ready to eat the city! Purchase a ticket here.

Join Bold Fork Books for an evening of conversation about Omi Hopper's debut cookbook, COOKING CON OMI: A Love Letter to Puerto Rican Home Cooking.

The Old Town Boutique Community is bringing back one of Alexandria's favorite summer traditions with the annual Alexandria Sidewalk Sale for its 17th year. During the two-day event, more than 30 independent boutiques throughout Historic Old Town Alexandria will bring their best summer merchandise outdoors, offering shoppers the season's biggest discounts on fashion, accessories, home décor, books, gifts, children's items, and more. Set among the neighborhood's historic brick-lined streets just minutes from Washington, D.C., the open-air shopping event invites visitors to explore locally owned businesses, discover one-of-a-kind finds, and enjoy special promotions while supporting Alexandria's vibrant small business community.

The 13th Annual Georgetown Shuck It! Beer & Oyster Festival returns to Tony & Joe's on Saturday, October 17, 2026, from 1:00 to 5:00 p.m., bringing together fresh oysters, local craft beverages, and live entertainment along the Georgetown waterfront. Guests ages 21 and older can enjoy freshly shucked and grilled oysters from local suppliers, locally brewed beers, regional wines, traditional BBQ favorites, and live music throughout the afternoon. Tickets are $82.50 and a valid ID is required for entry. Click HERE to grab your tickets.