Flights of Fancy Holiday 2025 Edition

Downtown New Haven sparkles a little brighter each holiday season thanks to Flights of Fancy, the city’s signature night of sipping, shopping, and tasting. Guests wander through favorite small businesses such as The Wine Thief, Strange Ways, dwell and more, enjoying bites and sips along the way, and discover gifts or maybe a little something just for themselves. The Holiday Edition adds exclusive discounts that make early gift shopping feel more like a festive night out than a to-do list.

Over a decade old, Flights of Fancy has evolved,

exploring new neighborhoods, restaurants, and experiences, yet its core remains the same: food, fashion, and wine. This year, festivities begin at Jack’s Bar & Steakhouse, where guests register, enjoy themed tastings, and receive a 25 percent dining coupon in their swag bag. Newcomers like Grails, downtown’s only record shop, add fresh energy to the mix, welcoming visitors into their brand new Chapel Street space.

Mark your calendars for Thursday, November 20, 2025, from 4:30 to 8:30 PM. Flights of Fancy is more than a night of fun; it is a toast to New Haven’s local businesses, charm, and holiday cheer.