Sip, Shop & Discover Downtown: Flights of Fancy Returns November 19

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Holiday shopping with a glass of wine in hand? That’s the idea behind Flights of Fancy, Downtown New Haven’s popular shopping, wine and food crawl. Returning Thursday, November 19, the holiday edition brings together independent shops, curated wine tastings, local bites and special promotions for an evening that makes checking off your gift list a little more fun.

Presented by Town Green District, Flights of Fancy encourages visitors to explore Downtown’s shopping districts, discover businesses they might otherwise overlook and make a night of it.

We caught up with the Town Green District team to find out what makes Flights of Fancy a Downtown favorite and what’s planned for this year’s holiday edition.

For someone who’s never been to Flights of Fancy, what makes it such a fun way to spend an evening Downtown?

Flights of Fancy is a delicious excuse to explore Downtown New Haven! Pick up your souvenir tasting glass and event bag, then make your way between participating shops, sampling wines curated by The Wine Thief and enjoying bites from local restaurants. Along the way, you’ll discover businesses you may have walked past countless times without stepping inside. Bring friends or come solo, compare your favorite finds and keep the evening going with dinner Downtown.

Holiday shopping doesn’t usually involve wine tastings and a night out with friends. How does Flights of Fancy make the experience a little more fun?

Forget the usual holiday-shopping rush. Flights of Fancy turns gift hunting into a night out, with local shops, good company and plenty of opportunities to find something you won’t see online or in a big-box store. Whether you’re shopping for someone on your list or treating yourself, it’s a chance to find gifts with a little personality. And the special shopping discounts are an added bonus.

What’s in store for the November 19 edition, and what makes this one special?

This year’s Holiday Edition kicks off at a new Downtown location, ZINC Garden Lounge. Check in, enjoy live jazz and your first food tasting from ZINC, then head out to explore Downtown.

This year, guests will receive NHV-branded cotton tote bags, replacing the previous nonwoven bags. There’s also a new opportunity to give back through a raffle for a $250 Wine Thief gift card. Raffle entries are $5, with all proceeds supporting New Reach and its work addressing homelessness, housing instability and food insecurity in New Haven.

For anyone who wants to enjoy the shopping and food without wine tastings, a discounted “Hold the Wine” ticket is also available.

Flights of Fancy: Holiday Edition takes place Thursday, November 19. Click here to purchase tickets.

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