Holidays in downtown New Haven: a treat for your senses (and pocketbook)

Downtown New Haven will be a treat for the senses this holiday season, hosting an array of free activities, shopping opportunities, and dining options.
holidays downtown

Ah, the sounds of the season: the sweet strains of familiar carols, the clop of hooves along city streets, and the hearty “Ho, ho, ho” of a certain bearded gentleman.

Downtown New Haven will be a treat for the senses this holiday season, hosting an array of free activities that will include roaming carolers and other musical entertainment, horse-drawn carriage rides, and storytelling with Santa.

There will also be ice-carving demonstrations, complimentary food and wine tastings, a hot cocoa contest, craft activities for the family, free parking, and giveaways — not to mention shopping discounts, a host of dining options, and scores of photo opportunities.

Below is detailed information regarding each event, which can also be found online at the Shops at Yale website.

The events are sponsored by The Shops at Yale, a coalition of retailers and restauranteurs in the Chapel Street Historic and Broadway Districts in New Haven, and by University Properties, which manages Yale’s commercial properties and is committed to enhancing the quality of life in New Haven through the development of high-quality retail and office environments and the revitalization of surrounding neighborhoods.

Free four-hour parking

Nov. 29-Dec. 24

Enjoy free four-hour parking with a $30 or more purchase from any of The Shops at Yale retailers. The free parking offer is available seven days per week at the following surface lots: 56 Broadway, across from L.L. Bean; 255 Crown St., behind Union League Café; and 161 York St., behind Derek Simpson Goldsmith. Customers simply show their store receipt to the parking lot attendant when exiting.

Black Friday & Small Business Saturday

Nov. 29-30, noon-4 p.m.

Roaming greeters will be out on Chapel Street and Broadway on Friday and Saturday with special discounts to retailers at The Shops at Yale. In addition, greeters will have giveaways for customers with a shopping bag from any retailer at The Shops at Yale, including $10 gift cards to downtown merchants, free totes, and more.

On Small Business Saturday, enjoy popcorn, giveaways, and raffle opportunities at the New Haven Visitor’s Center, 1000 Chapel St., noon-4 p.m., sponsored by Town Green District. The Shops at Yale will host an ice-carving demonstration in front of Wave Gallery 1-3 p.m. at 1046 Chapel St.; storytelling with Santa at The Yale Bookstore 1-3 p.m. at 77 Broadway; a craft activity at Hull's Framing 3-5 p.m. at 1144 Chapel St.; roaming Yuletide Carolers 1-5 p.m.; and outdoor holiday horns on Chapel Street 2-4 p.m.

The New Haven Green covered in snow, looking towards Chapel Street
(Photo credit: Michael Marsland)

A Taste of Chapel — Holiday Series

Thursdays Dec. 5, 12 and 19, 4:30-7 p.m.

Complementary local food and wine tastings, exclusive shopping discounts and more on the following days and locations:

  • Dec. 5, dwell New Haven, 1022 Chapel St. The Union League Café is pairing wine that was specifically selected by their sommelier with a variety of gourmet cheeses from Arethusa Farm Dairy.
  • Dec. 12, Raggs for Men & Women, 1020 Chapel St.
  • Harvest Wine Bar & Restaurant is highlighting their house label wine, which will be complemented by a seasonal appetizer pairing from South Bay Restaurant.
  • Dec. 19, Wave Gallery, 1046 Chapel St. Pacifico is pairing wine that was specifically selected by their wine expert with chocolate truffles from Wave Gallery.

Ice carving competition & a cappella concert

Dec. 7, noon-4 p.m.

Broadway Island, 56 Broadway (across from L.L. Bean)

Six professional ice carvers will each transform three 900-pound blocks of ice into sculptures. There will be live performances by a cappella groups, including The Yale Alley Cats, Whim ’n Rhythm, The New Blue, Proof of the Pudding, Yale Out of the Blue, Red Hot & Blue, Southern Connecticut State University’s NOTEorious, and more.

Hot cocoa contest

Dec. 7, noon-3 p.m.

Top restaurants in New Haven will compete to see whose hot cocoa wins the hearts of shoppers. Stops will be located inside retailers on Broadway, and winners will be chosen by a people’s choice voting system. Voting cards will be available at The Shops at Yale table on Broadway Island. Limited to the first 250 people. There will also be a chance to enter The Shops at Yale raffle to win gift cards and other prizes. Free event parking is available at the 150 York St. Garage, 11 a.m.-7 p.m. The Shops at Yale staff will validate parking tickets during the event.

Ice-carving demonstrations

Nov. 29, 30; Dec. 1, 8, 15 and 22, 1-3 p.m.

1046 Chapel St., in front of Wave Gallery

Watch as professional ice carvers from Ice Matters in Cheshire, Connecticut take two 300-pound solid blocks of clear ice, each measuring 40” tall x 20” wide, and transform them into a reindeer (on Nov. 29), the Elm City Elf (Nov. 30), snowflake selfie frame (Dec. 1), bulldog (Dec. 8), train (Dec. 17) and a Santa on a chimney (Dec. 22).

Hop-on/hop-off horse-drawn carriage rides

Sundays, Dec. 1, 8, 15 and 22, and Saturday, Dec. 7, noon-4 p.m.

Enjoy free horse-drawn carriage rides this holiday season in downtown New Haven. Hop-on/Hop-off at the corner of College and Chapel streets (across from Claire’s Corner Copia) and the corner of York and Elm streets (across from Patagonia and GANT).

Santa visits the Yale Bookstore in 2018.

Storytelling with Santa

Nov. 30, Dec. 7, 14 and 21, 1-3 p.m. at The Yale Bookstore, 77 Broadway, with treats provided by Katalina’s Bakery
Dec. 1 and 22, 1-3 p.m. at Willoughby’s Coffee & Tea, 194 York St.
Dec. 8 and 15, 1-3 p.m. at Claire’s Corner Copia, 1000 Chapel St.

Santa will visit The Shops at Yale and read various stories to children. Free snacks will be provided.

Free weekend craft activities

Nov. 30, Dec. 7, 14 and 21, 3-5 p.m. at Hull’s Art Supply, 1144 Chapel St.
Dec. 1, 8, 15 and 22 at The Yale Bookstore, 77 Broadway, 2-4 p.m.

Family-friendly craft projects, such as holiday card making, rock painting, gel plate painting, and more.

Andy Wolf holiday TUBULATION series

Nov. 29, 30, and Dec. 1, 7, 8, 14, 15, 21 and 22, 2-4 p.m.

Enjoy the sounds of outdoor holiday horns on Chapel Street.


Nov. 29, 30, and Dec. 7, 14, 21 and 22, 1-5 p.m.

Connecticut Yuletide Carolers will perform live at The Shops at Yale along Chapel Street and Broadway. The traditionally garbed Victorian Carolers will perform songs of the season.

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