Autumn on the Upper East Side has a charm all its own: tree-lined streets glowing with golden leaves, boutique windows dressed for the holidays, and a sense of cultural elegance in the air. For those who savor high society, world-class art, and time-honored traditions, this season offers a curated lineup of can't-miss events that showcase the best of New York City's most sophisticated neighborhood. Whether you're a longtime resident or an occasional visitor with impeccable taste, here's your guide to the Upper East Side's most stylish fall and early winter happenings.
The Met Fall Festival 2025
October 18 at The Metropolitan Museum of Art (The Met)
There's no better place to kick off the season than at The Met Fall Festival, a lively and immersive celebration for art lovers of all ages. Held throughout the museum's expansive halls and outdoor plazas, this annual festival invites guests to create art, enjoy live performances, and explore current exhibitions. Whether you're exploring masterpieces in the European Wing or joining a drop-in painting session with the kids, the atmosphere is festive, inclusive, and uniquely Met. It's a day when art leaves the frame and enters the heart of the community.
There's no better place to kick off the season than at The Met Fall Festival, a lively and immersive celebration for art lovers of all ages. Held throughout the museum's expansive halls and outdoor plazas, this annual festival invites guests to create art, enjoy live performances, and explore current exhibitions. Whether you're exploring masterpieces in the European Wing or joining a drop-in painting session with the kids, the atmosphere is festive, inclusive, and uniquely Met. It's a day when art leaves the frame and enters the heart of the community.
The Met Pajama Party
October 23 at The Met’s Temple of Dendur and Engelhard Court
Art meets enchantment at The Met Pajama Party, an imaginative, Halloween-inspired evening that transforms the museum into a whimsical after-dark experience. Guests, young and old, are encouraged to dress in pajamas or costumes and enjoy themed art activities, a curated seasonal menu, and live entertainment beneath the stars of the Temple of Dendur. With the museum's grandeur as the backdrop, this family-friendly soirée feels equal parts museum night and childhood dreamscape.
Art meets enchantment at The Met Pajama Party, an imaginative, Halloween-inspired evening that transforms the museum into a whimsical after-dark experience. Guests, young and old, are encouraged to dress in pajamas or costumes and enjoy themed art activities, a curated seasonal menu, and live entertainment beneath the stars of the Temple of Dendur. With the museum's grandeur as the backdrop, this family-friendly soirée feels equal parts museum night and childhood dreamscape.
Wollman Rink Opens for the Season
October 24 at Wollman Rink, Central Park South
There's a certain magic to skating under the open sky in Central Park, and Wollman Rink delivers it with timeless flair. Located in the southwestern corner of Central Park, the rink reopens this weekend for its 2025–2026 season, complete with skate rentals, lessons, and seasonal concessions. As Manhattan's skyline shimmers in the distance, it's the perfect spot for a romantic date, a family afternoon, or a solo glide beneath the city's changing leaves. In addition, themed nights and live performances are scheduled throughout the season.
There's a certain magic to skating under the open sky in Central Park, and Wollman Rink delivers it with timeless flair. Located in the southwestern corner of Central Park, the rink reopens this weekend for its 2025–2026 season, complete with skate rentals, lessons, and seasonal concessions. As Manhattan's skyline shimmers in the distance, it's the perfect spot for a romantic date, a family afternoon, or a solo glide beneath the city's changing leaves. In addition, themed nights and live performances are scheduled throughout the season.
Madison Avenue Fall Gallery Walk
October 25 on Madison Avenue from East 57th to 86th Streets
For art aficionados, the Madison Avenue Fall Gallery Walk is a refined Saturday escape. This one-day-only event, hosted by ARTnews, welcomes guests into dozens of the Upper East Side's top galleries for exclusive exhibitions and guided talks with artists and curators. Whether you favor modern masters, postwar minimalism, or contemporary sculpture, the walk offers an intimate look into the city's dynamic art market. No tickets required; just good shoes and a sharp eye.
For art aficionados, the Madison Avenue Fall Gallery Walk is a refined Saturday escape. This one-day-only event, hosted by ARTnews, welcomes guests into dozens of the Upper East Side's top galleries for exclusive exhibitions and guided talks with artists and curators. Whether you favor modern masters, postwar minimalism, or contemporary sculpture, the walk offers an intimate look into the city's dynamic art market. No tickets required; just good shoes and a sharp eye.
Spooky City at the Museum of the City of New York
October 31 at The Museum of the City of New York, Fifth Avenue at 103rd
For a Halloween celebration that blends history, creativity, and fun, Spooky City at MCNY hits the mark. This festive event includes a scavenger hunt through the galleries, arts and crafts, harvest-themed games, and special Halloween story time for young children. It's an educational and interactive afternoon that encourages families to explore the museum's vibrant exhibits while enjoying a taste of New York's spirited Halloween culture.
For a Halloween celebration that blends history, creativity, and fun, Spooky City at MCNY hits the mark. This festive event includes a scavenger hunt through the galleries, arts and crafts, harvest-themed games, and special Halloween story time for young children. It's an educational and interactive afternoon that encourages families to explore the museum's vibrant exhibits while enjoying a taste of New York's spirited Halloween culture.
Miracle on Madison Avenue
December 6 in the Madison Avenue Shopping District
A glittering holiday tradition for nearly four decades, Miracle on Madison Avenue is part shopping spree, part charitable event, and all-around holiday delight. Participating boutiques and luxury retailers donate 20% of the day's sales (up to $15,000 per store) to support MSK Kids, the pediatric programs at the Memorial Sloan Kettering Cancer Center. Expect carolers, festive windows, warm beverages, and the chance to mingle with the MSK Caring Canines therapy dogs while checking off your holiday gift list with purpose and style.
A glittering holiday tradition for nearly four decades, Miracle on Madison Avenue is part shopping spree, part charitable event, and all-around holiday delight. Participating boutiques and luxury retailers donate 20% of the day's sales (up to $15,000 per store) to support MSK Kids, the pediatric programs at the Memorial Sloan Kettering Cancer Center. Expect carolers, festive windows, warm beverages, and the chance to mingle with the MSK Caring Canines therapy dogs while checking off your holiday gift list with purpose and style.
Holiday Market at the Museum of the City of New York
December 6 and 7 at the Museum of the City of New York
Back by popular demand, the Holiday Market at MCNY offers a curated selection of artisan goods, crafts, and unique gifts from makers across all five boroughs. Held in partnership with Brooklyn Pop-Up, this festive indoor market elevates holiday shopping, set against the cultural backdrop of one of the city's most beloved institutions. Saturday also features Gingerbread NYC Community Day, showcasing gingerbread creations from bakeries across the city. It's free to attend and ideal for anyone seeking one-of-a-kind gifts with a New York touch.
Back by popular demand, the Holiday Market at MCNY offers a curated selection of artisan goods, crafts, and unique gifts from makers across all five boroughs. Held in partnership with Brooklyn Pop-Up, this festive indoor market elevates holiday shopping, set against the cultural backdrop of one of the city's most beloved institutions. Saturday also features Gingerbread NYC Community Day, showcasing gingerbread creations from bakeries across the city. It's free to attend and ideal for anyone seeking one-of-a-kind gifts with a New York touch.
The Met's Art & Artists Gala
December 10 at The Met’s Great Hall
The season concludes in true Upper East Side fashion with a black tie benefit. The Art & Artists Gala at The Met is one of the museum's most elegant affairs, celebrating the visionary artists and exceptional works that define its permanent collection. Held in The Great Hall, this black-tie evening includes a cocktail reception, seated dinner, and live performance, all in support of The Met's acquisitions fund. For collectors, philanthropists, and art patrons, it's a night not to be missed.
Discover More of the Upper East Side Trusted Real Estate Partner
The Upper East Side is a cultural powerhouse throughout the fall, blending elegance, creativity, and civic-minded celebration in equal measure. From landmark galas to kid-friendly Halloween nights, these events remind us why this neighborhood continues to captivate both lifelong New Yorkers and those just discovering its charms.
If you're seeking even more of what the Upper East Side has to offer, including the neighborhood's landmark real estate offerings, contact the Coldwell Banker Warburg team today to begin your NYC real estate journey.
