Boundary Stone hosts its annual Atlas Toy Drive Fundraiser, welcoming Santa to the pub on December 17. Adults who bring an unwrapped toy donation will receive a free Atlas Brew Works beer. Santa will be available for photos from 5 to 8 p.m., with tickets priced at $10 each; all proceeds benefit St. Baldrick's Foundation, a nonprofit dedicated to pediatric cancer research. More info here.

Waldorf Astoria Washington DC hosts its Holiday Spectacular, transforming the historic hotel into an elegant, festive escape for a late-afternoon holiday outing with the family. Guests can enjoy seasonal bites inspired by the hotel’s signature afternoon tea, sip on drinks from the holiday mimosa bar, and warm up with decadent hot chocolate from the specialty station. The event features live entertainment, lavish holiday décor, and complimentary professional portraits by the tree, printed onsite as keepsakes. Santa will also make an appearance, adding a classic touch to family portraits. More info here.

The 2026 DC Travel & Adventure Show returns to the Walter E. Washington Convention Center January 17–18, bringing nearly 300 destinations and travel suppliers together under one roof. This year’s event features celebrated travel personalities Rick Steves and Samantha Brown, alongside an expansive array of exhibitors representing Italy, South Africa, the Caribbean, and top North American getaways. Attendees can explore the new Dive and Water Sports Pavilion, meet one-on-one with global travel experts, and enjoy dozens of educational sessions covering everything from solo travel and packing tips to local immersion and budget-friendly planning. With exclusive show-only deals, expert insights, and opportunities to personalize future trips, the DC Travel & Adventure Show offers an immersive weekend designed to inspire every type of traveler. Tickets start at $16, with free admission for children 16 and under and complimentary entry for active-duty military plus four family members. Click HERE to grab your tickets.

Medium Rare rings in 2026 with its beloved New Year’s Day Pajama Brunch, returning on Thursday, January 1st, from 10:00 AM to 5:00 PM at all DMV-area locations. Guests are invited to start the new year in comfort and style by arriving in their coziest, classiest, or most creative pajamas for a chance to win $100 Medium Rare gift cards in four categories: Best Family Jammies, Most Creative Pajamas, Best Group Theme, and Most Festive PJs.While judges discreetly circulate the dining room, brunchgoers can enjoy Medium Rare’s signature prix fixe offerings, including Steak & Eggs, the Famous Benedict, overnight-soaked French Toast, and bottomless mimosas.A festive, cozy, and crowd-favorite tradition, the Pajama Brunch offers a cheerful start to the year at one of the region’s most beloved brunch destinations.

Beauty Champagne & Sugar Boutique has announced the launch of Grape School, a new monthly wine education series debuting in January 2026 in National Landing, VA. Held on the first Monday of each month from 6:30–7:30 PM, the program offers an approachable and engaging way for guests to explore a different grape variety through curated wine tastings, paired bites, take-home notes, special guests, and the boutique’s signature playful atmosphere. “Each month we spotlight a single grape so guests can truly taste its personality, its history and its range,” says owner Zena Polin. Designed for everyone from curious newcomers to seasoned sippers, the series fosters connection through wine, learning, and community. The January–May lineup features expert-guided sessions on Malbec, Nebbiolo, women-led wineries, Grüner Veltliner, and Sagrantino—complete with a May the Fourth twist. Tickets are $35 per person, with extremely limited seating. Email Zena at [email protected] to pay and reserve your spot.

The National Press Club presents An Enchanted Holiday Tribute —an elegant and inspiring evening that blends world-class performance with festive seasonal celebration. Featuring the powerful artistry of The Washington Tattoo and the refined voices of the Washington Opera Society, the event elevates traditional holiday programming into an unforgettable, culturally rich experience.Audiences will enjoy beloved holiday classics, stirring musical tributes, and a moving salute to the Armed Forces, culminating in a joyful holiday sing-along. Special guests include Maestro Jason Tramm (conductor), Robin Phillips (narrator), tenor Jeremy Brauner, and soprano Christina Major.VIPs and Sponsors receive early admission at 6:30 PM, including a champagne reception, followed by General Admission at 7:00 PM. The performance begins at 7:30 PM.Ticket Options:• General Admission – $75: Entry at 7:00 PM; concert only• VIP – $125: Early entry at 6:30 PM plus champagne reception• Sponsor – $800 (for two guests): Early entry at 6:30 PM, champagne reception, program acknowledgement, and tax benefitA sophisticated and heartfelt holiday experience, An Enchanted Holiday Tribute invites guests to celebrate the season through music, elegance, and the spirit of gratitude.More info here.

Le Diplomate celebrates the season with a festive Mrs. Claus Brunch on Saturday, December 20th, from 10:00 AM to 4:00 PM. Families are invited to enjoy a cheerful day of dining and holiday activities as the beloved brasserie transforms into a charming winter wonderland for one day only.Guests can indulge in complimentary mini chocolate chip financiers and cocoa, along with a variety of family-friendly indoor activations. Highlights include a Mrs. Claus & Elf table, a “Letters to the North Pole” station where guests can write notes to drop into Le Diplomate’s holiday mailbox, face painting, balloon art featuring seasonal characters, and a Pixel Strut mobile photo booth to capture the magic.Designed for both children and adults, the Mrs. Claus Brunch offers a warm, festive, and immersive holiday experience in one of D.C.’s most iconic dining destinations. More info here.

Chef Mikko welcomes the community to celebrate the season at the Mikko Holiday Market, returning for three festive weekends on December 6–7, 13–14, and 20–21. Open from 11:00 AM to 6:00 PM, the market offers a cozy Nordic-inspired holiday experience, with brunch service available from 9:00 AM to 4:00 PM on Saturdays and Sundays.Guests can browse a curated selection of unique Nordic treats and gifts, including handcrafted chocolates made in-house by Chef Mikko’s team, freshly baked Scandinavian pastries, traditional glögg (mulled wine), and a variety of specialty goods available only during the holiday season. Each weekend features new flavors, festive items, and culinary surprises.Designed to bring together neighbors, food lovers, and holiday shoppers, the Mikko Holiday Market highlights Chef Mikko’s Nordic heritage and warm hospitality. Visitors can enjoy brunch, pick up seasonal gifts, or savor festive treats in a welcoming and community-focused atmosphere.

Families are invited to ring in the new year at the Pajama Jam Family Dance Party on December 31st from 8:00 PM to 12:30 AM. Guests are encouraged to wear their coziest pajamas for an evening filled with festive fun, including a delicious dinner buffet, lively music from DJ Nico, family games, and a special New Year’s countdown.The celebration culminates in a midnight balloon drop, making it a magical way for families to welcome 2026 together in a joyful and energetic atmosphere.

Salamander Middleburg invites families to enjoy a series of festive Family Movie Nights inside the resort’s cozy screening room this holiday season. On Christmas Eve, guests can settle in for a showing of the holiday favorite Elf. On Christmas Day, the beloved classic It’s a Wonderful Life will be screened. The series concludes on December 30th with the animated winter adventure Happy Feet.Perfect for families looking to relax and enjoy seasonal entertainment together, each movie provides a warm and joyful way to unwind during the holidays.