Port Washington welcomes shoppers of all ages with 2 Saturdays that make shopping local an experience you won’t want to miss. Participating stores provide special offers and treats while you shop. FREE Trolley rides transport shoppers. A full “Shoppertainment” schedule and live performances at multiple locations. Schedule details will be posted on the Try Port First app. Main Street parking is FREE from November 26, 2025 through January 1, 2026.
Saturday, November 29 is Port Holiday Magic on Small Business Saturday
Start the Holiday Magic season with Small Business Saturday. Santa rings in the festivities from the firetruck at 12 noon. Participating businesses will have deals and treats – check the Try Port First app for a list of the stores and their special offers and look for the red bows on the store fronts. Follow the singing Toy Soldiers as they visit stores on Main Street.
Saturday, December 6 is Port Holiday Magic II – “SHOP LOCAL, GIVE LOCAL.”
Visit Santa at the Landmark on Main Street. Enjoy live music and refreshments while you peruse the Give Local Hub. We are bringing local non-profit orgs under one roof to make giving easy. Plus, participating businesses become collection sites for the very successful “Make a Child Smile Toy, Food & Diaper Drive.” All donations will be distributed locally.
Sing Sip and Stroll, Saturday, December 2 – 4:30 pm. Follow the designated map of participating businesses who will provide sample sips for $2 each. Join the strolling caravan and sing along with Santa. We will provide the words so you can sing along and receive a commemorative cup if you’re among the first 40 participants. Free Hop On/Hop Off trolley during the event.
All Week Long
RadioPW plays the sounds of the season. Port Washington’s own hyperlocal streaming station provides updates and announcements as well as tunes to set a festive mood. Tune in https://s3.radio.co/s0d381dadb/listen
Window Decorating Contest. Businesses throughout town display their holiday spirit with the window decorating contest. Final awards for best painted and best decorated will be announced. The trolley riders will enjoy a special sing-a-long on this Saturday.
New This Year
Port Holiday Magic Selfie Challenge: Visit. Snap. Send. Win gift cards & baskets full of local magic! From Saturday to Saturday, Visit 3 local participating businesses. Snap a selfie with the handheld prop. Send the selfie shots to PortHolidayMagic@gmail for a chance to Win. Details posted at each participating business location.
Details will be posted on the Try Port First app. Go to your app store, search Try Port First to download. Click EVENTS and see each date for details. You can see the full list of participating businesses and the trolley stops HERE.
Port Holiday Magic is sponsored by Precision Works, Inc. and Port Washington BID. The events are hosted by the Port Washington Chamber of Commerce, Port Washington BID, Residents Forward, and Landmark on Main Street with special support from the Town of North Hempstead and the Port Washington Police District.