Washington D.C.'s Best Fall and Winter Celebrations
As the vibrant hues of autumn sweep across the nation's capital and the crisp air ushers in the cozy charm of winter, Washington, D.C., transforms into a spectacular backdrop for an array of unforgettable festivals and events. Nestled at the nexus of Dupont Circle, the West End, and Georgetown, The St. Gregory Hotel offers an unparalleled haven from which to immerse yourself in this seasonal splendor. Our luxurious accommodations, thoughtful amenities, and prime location ensure that your stay is not just a visit, but an experience - a sophisticated retreat perfectly complemented by the city's festive spirit.
H Street Festival
September 9, 2025
Just a short distance from The St. Gregory, the H Street Festival ignites the Northeast corridor with an explosion of energy. This massive, single-day event sprawls across 11 blocks, offering live music across multiple stages, captivating dance performances, and an endless array of food vendors serving up delectable treats. Wander through the bustling crowds, discover unique artisan crafts, and soak in the infectious enthusiasm that defines this iconic neighborhood celebration. It's a true reflection of D.C.'s diverse and dynamic spirit, providing a perfect opportunity to experience the city's artistic heartbeat.
DMV Farm Festivals
Late September Through October 2025
For those yearning for a taste of rustic charm and wholesome family fun, the numerous Farm Festivals surrounding D.C. are an absolute must. Farms like Cox Farms and Butler's Orchard offer quintessential fall experiences, inviting you to pick your own pumpkins, enjoy fresh cider, and embrace the simple joys of the season. The DMV area's fall farms offer a refreshing day trip that creates lasting memories for guests of all ages.
Adams Morgan Day
September 14, 2025
Step into one of D.C.'s most beloved and longest-running traditions with Adams Morgan Day. This annual neighborhood festival showcases the eclectic charm of Adams Morgan, featuring a delightful mix of local businesses, talented artists, and community organizations. Stroll along 18th Street, browse unique wares, enjoy live entertainment, and savor the diverse culinary offerings that reflect the neighborhood's multicultural essence. It's a wonderful opportunity to experience a slice of authentic D.C. life and witness the strong community spirit that thrives within its vibrant enclaves.
Because They're Funny Comedy Festival
October 10-12, 2025
For an evening filled with wit and laughter, the Because They're Funny Comedy Festival is a standout. This festival proudly spotlights BIPOC comedians, offering a diverse and insightful range of comedic voices. From headline shows featuring established stars to showcases for rising new talent, this festival provides a platform for powerful storytelling and uproarious humor. It's a chance to engage with contemporary comedy that is both entertaining and thought-provoking.
DowntownDC Holiday Market
November 21-December 23, 2025
The heart of the holiday season beats strongly at the DowntownDC Holiday Market. This enchanting outdoor market, set against the stunning backdrop of the National Portrait Gallery and American Art Museum, is a treasure trove of unique gifts, artisan crafts, and festive delights. Browse dozens of vendors, discover one-of-a-kind presents for loved ones, and savor an array of delicious food and beverages. The air is filled with the scent of roasted nuts and warm spices, while live entertainment adds to the joyful atmosphere. It's the perfect place to find that special something and soak in the true spirit of the holidays.
Your Perfect Seasonal Retreat: The St. Gregory Hotel
Whether you're seeking the lively energy of a fall street festival or the enchanting glow of a winter wonderland, The St. Gregory Hotel is your perfect base for experiencing the best of Washington D.C.'s seasonal celebrations. Book your stay with us and discover a sophisticated sanctuary amidst the capital's captivating charm. When you stay more, you save more. Get up to 20% savings when you stay 3 nights or more.