Friday, November 27, 2015 ~ 5 - 8 p.m. Parade at 6 p.m.

The Holiday Stroll is a cherished tradition which kicks off the holiday season in Whitefish Bay on the Friday following Thanksgiving. Hosted by the Whitefish Bay Business Improvement District, the Holiday Stroll is an event for the whole community and a way for the merchants to thank everyone for their support throughout the year. A family-friendly affair with a relaxed atmosphere, the Holiday Stroll is a perfect start to the season with music, refreshments and more as you revisit refined shopping with your friends and loved ones during a stroll along Silver Spring Drive this holiday season!

Holiday Stroll Sponsors
Many, many thanks to all who make great events like the Holiday Stroll possible. It really does take a village... from the people in the parade, the businesses hosting open houses and a holiday extravaganza, the village public works department that makes our street look so great, to the many families that come out to enjoy the festivities.
Presenting Sponsors

BMO Harris Bank

Ellenbecker Investment Group

Ideal Property Management

Sendikís Food Market

Yellow Wood

Major Sponsors


Elements Massage

Massage Envy
Mindy DeHate Real Estate Division of Keller Williams North Shore


PNC Bank

United Methodist Church of Whitefish Bay

Community Partners
             First Stage Touring Company

             Milwaukee Ballet School

Village of Whitefish Bay

Whitefish Bay Civic Foundation

Community Sponsors
              Bay Ridge Consulting             
              Beaumont Place

              Powers Realty Group
Three Wishes
              Andrew Chevrolet
              Fitness Together
              Herslof Opticians
              Indulge Studios
              Penzeys Spices
 Realty Executives

 RedCap Luggage & Gifts

 Winkie's Toys & Variety


Parade & Entertainment
The seasonal celebration features our cherished parade, which celebrates the joy of the season as well as celebrating our great community. We have music, Dancing Grannies, racing sausages, Alaskan Malamutes, scout troops, media, and so much more... including Santa himself, in his sleigh pulled by his reindeer, Cupid and Holly. It's an evening not to miss!

After the parade, there are plenty of family-friendly activities, including scenes from The Nutcracker performed live in store windows, a tree lighting ceremony at Sendik's Food Market and free entertainment, including music and dance performances, pony and train rides, meet and greet with sled dogs, and a visit with Santa at BMO Harris Bank!
  • Tree Lighting at ~ 7pm after the parade at Sendik's Food Market
  • Holiday DJ music and live music performed by the First Stage Touring Company and a dance performance by Bella Via Dance Studio.
  • Milwaukee Ballet scenes in store windows.
  • First Stage Touring Company at Associated Bank.
  • Visits with Santa at BMO Harris Bank after the parade. Also live music provided by a Whitefish Bay High School string quartet.
  • Open Houses at stores along Silver Spring Drive
  • Pony rides on the east end of Silver Spring Drive after the parade, across the street from (and sponsored by) Ellenbecker Investment Group
  • Train rides by the Fox Bay Building sponsored by Elements Massage.
  • Meet and Greet with the Door County Sled Dogs, sponsored by Yellow Wood Gear. The dogs will be stationed on Berkeley Boulevard after the parade adjacent to the our newest retailer, Yellow Wood.

Shopping Specials and Store Open Houses
Discover shopping specials and conveniently cross things off your holiday list over incredible treats throughout the day and into the evening as shops extend their hours. Some shops are even extending their specials over the weekend in honor of Small Business Saturday.  Check back soon... we've been adding specials regularly.

For those of you already planning your holiday shopping, we already have some great deals posted below!

  • Associated Bank - Enjoy caroling by the First Stage Touring Company. First Stage is performing a Charlie Brown Christmas this year.
  • BMO Harris Bank - Visit Santa after the parade. Live music provided by a Whitefish Bay High School string quartet.
  • Breadsmith - Live ballerinas from the Nutcracker in store windows during the Holiday Stroll.
  • City Market Cafe - LIVE music during the Holiday Stroll. Enjoy the sounds and talents of Whitefish Bay High School's band.
  • Dan Fitzgerald Pharmacy - Fitzgerald Pharmacy's Private Label Black Friday Sale!! Buy one DFB Private Label product and Get one 50% off of equal or lesser value.  Black Friday sale valid 11/27-11/29.  All previous sale excluded.  Valid on in stock products only. Live ballerinas from the Nutcracker in store windows during the Holiday Stroll.
  • Elements Massage - We all know someone who deserves to feel amazing. Give the gift of an Elements Massage™ Gift Card and treat them to a re-energizing therapeutic massage. Itís simply the best massage, guaranteed. Special Holiday Offer: Buy One Get One Free - $89 for (2) Two 1 Hour Gift Cards (Reg $178).  Hurry offer expires Sunday, 11/29/15 and gift cards are good for one year from purchase. Stop by during the Holiday Stroll for complementary chair massage, festive food and beverages.  Free gift wrap on all purchases.

  • Fitness Together - We will be offering BOGO Holiday Stroll Special. Buy 1 month, Get 1 FREE!

  • Fringe Fine Furnishings - SIP, SHOP AND GET FRINGED! Stop in and see the furniture store everyone is talking about! Join us at Fringe on Friday, November 27th from 9am to 5pm during Whitefish Bayís Holiday Stroll and enjoy a complimentary glass of wine while you shop. Receive your choice of a Woodfire or Balsam & Cedar candle tin while they last. Come #getfringed!

  • Gallery 505 & The Great Frame Up - Warm up with treats and hot cider while viewing our art. We also will have LIVE music by Peter Donalds. Also, see artist Curt Crain live-paint!! Live ballerinas from the Nutcracker in store windows during the Holiday Stroll.

  • Mathnasium - Live ballerinas from the Nutcracker in store windows during the Holiday Stroll. Will be serving cookies and hot chocolate during the Holiday Stroll to keep you warm.

  • New Options Salon & Spa - 20% off salon products including Aveda, Sebastian, MoroccanOil and Bioelements.

    20% off all boutique merchandise including jewelry, handbags, accessories and fashion. Fri Nov 27 & Sat Nov 28. Live ballerinas from the Nutcracker in store windows. Live ballerinas from the Nutcracker in store windows during the Holiday Stroll.

  • Penzeys - Stop in out of the cold and enjoy a nice warm cup of mulled cider and a free gift!

  • Pure Barre - Stop in and take advantage of our retail and package specials!
  • RedCap Luggage & Gifts - With few exceptions ENTIRE STORE IS ON SALE! Enjoy delicious warm cider, nibble on a cookie and shop the many in-store bargains: Select Tumi 25% off, Briggs & Riley save $50 for every $350 B&R purchase, Leather Duffels up to 60% off, All Briefcases on sale! Jewelry boxes, Games, Pens, Handbags etc.. ALL ON SALE! We meet or beat every price on the internet, WE WILL NOT BE UNDERSOLD!- SHOP LOCAL~Also BLACK FRIDAY/SMALL BUSINESS SATURDAY SPECIAL: RedCap Luggage will be giving away free tablet cases (value up to $80.00 while supplies last!)

  • ReFresh Aesthetic Center - 20% off all skincare products and selected skin services.  Black Friday and Saturday.

  • Wagner Pediatric Dentistry - Live ballerinas from the Nutcracker in store windows during the Holiday Stroll.

  • Winkie's - LIVE music during Holiday Stroll

~~ Offers subject to change ~~