SHOP & STROLL

Join us for an evening of local shopping at the Holiday Shop & Stroll on Thursday, December 11th. 

Enjoy special discounts at participating stores and other festive happenings around Town from 6PM - 9PM!  And be sure to join us for the pre-event happy hour from 5PM - 6PM at the Fairfield University Store, Second Story, more information below!

Check off everyone’s wish lists and find the latest fashion apparel, home décor, jewelry, toys, sporting goods, dinner gift cards, best-selling books and more! 

All participating merchants will be listed below and scroll to learn more about our pre-event happy hour and our philanthropic partner

*The event is rain or shine with festive happenings subject to change*

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PHILANTHROPIC PARTNER

Each year, we work with a philanthropic partner to bring awareness to local cause. We’re excited to partner once again with the Fairfield University Student Alumni Association to collect teddy bears for their 27th Annual Teddy Bears with Love drive. Teddy bears will be delivered to children in area hospitals this holiday season. To learn more, visit their website.

We will be collecting bears during the following events:

Small Business Saturday Welcome Station at Greenfield Hill Commons

Saturday, November 29 from 10AM - 2PM at 75 Hillside Road

13th Annual Holiday Shop & Stroll Pre-Event Happy Hour

Thursday, December 11 from 5PM - 6PM

Teddy bears can also be dropped off at the Town of Fairfield’s Office of Community & Economic Development (611 Old Post Road, 2nd Floor Fairfield) during regular business hours Monday - Friday 8:30AM - 4:30PM now through December 11th.

Trolley Transportation

All Aboard! We’re excited to introduce the trolley, which will travel along Post Road between the Brick Walk Promenade and Heritage Square transporting attendees along the shopping route. The trolley will be running continuously throughout the event and will be making the following stops:

  • Fairfield University Store (1499 Post Road)

  • Brick Walk Promenade (1215 Post Road)

  • SHU Community Theatre (1420 Post Road)

  • Heritage Square (1700 Post Road)

Special thanks to Kleban Properties for their sponsorship of this year’s trolley!

Kleban Properties is a five-generation family business proudly developing and managing properties in Fairfield. We wish our tenants, customers and community a happy holiday!


PRE-EVENT HAPPY HOUR

Join us for the Holiday Shop & Stroll Pre-Event Happy Hour at the Fairfield University Store, Second Story from 5PM - 6PM!

There will be complimentary light bites and a cash bar serving beer, wine, prosecco, spiked seltzer, and a seasonal cocktail!

Be sure to stop by and pick up a holiday Fairfield Buy Local tote bag filled with goodies from local merchants (available while supplies last)!


PARTICIPATING MERCHANTS


PARTICIPATING SALONS & SERVICES


PARTICIPATING BARS & RESTAURANTS


PARTICIPATING ARTS & CULTURE


SPONSORS

Thank you to our sponsors of the 2025 Holiday Shop & Stroll!

Logo for Fairfield Connecticut Buy Local campaign with gazebo graphic.
Logo of Connect Fairfield, featuring stylized letters with colorful dots and circular design