Light Up Westbrook Holiday Event Series
Window Display Contest
Each year, to complement the beautiful downtown light display, Discover Downtown Westbrook hosts a Holiday Window Display Competition.
Businesses are encouraged to decorate their windows and participate in the friendly competition. Voting will be open to the public in December, and the winners will be announced and awarded the week before Christmas.
This is a free, no-registration-required opportunity to join in the holiday festivities and encourage people to enjoy Westbrook during the colder months. All of Westbrook’s storefront businesses are encouraged to join in!
The 2025 Holiday Window Display Contest is now over—click here to see this year’s winners! We had seven possible awards: Three People’s Choice awards and four Specialty Judges’ categories.
Thanks to everyone who decorated, voted, and shared online. We look forward to seeing the competition in 2026!
Holiday Market on the Common
DDW hosted the 2025 Westbrook Holiday Market at Westbrook Common as part of Light Up Westbrook. The market provides a way to gather people at Westbrook Common during the colder months, uplift local artists and makers, enjoy the fantastic downtown light displays, and support downtown businesses. Even in the cold and snow, Light Up Westbrook brings light and celebration to downtown with the help of our local community.
Special thanks to our vendors and entertainment: Versatile Vessels, To Ducky Crafts, Gilded and Forged, Sick Pig Designs, Fiya’sco, and Keith Prairie for his holiday music played on a hammered dulcimer. Be sure to check out these local entrepreneurs!
See you next year!
Buy Westbrook – Gift Giving Guide 2025!
Each year, Discover Downtown Westbrook creates a Gift Giving Guide to encourage #BuyWestbrook and support our local businesses. Many of Westbrook’s businesses offer truly amazing holiday gifts. This year, we have almost 30 Westbrook-based businesses in our Gift Giving Guide – check out the digital version below.
Printed Gift Giving Guides are distributed at holiday events throughout December. They are also found in stores, restaurants, and bars around town. Please support our local business ecosystem by shopping local this holiday season.
2025 Gift Giving Guide!
While visiting the lights and displays, enjoy dinner or a drink in downtown Westbrook!
While you are here, be sure to shop downtown or stop at one of our renowned eateries. Visit Portland Pie Westbrook, Fajita Grill, Westbrook House of Pizza, Blazes Burgers, China Villa, Casa Novello, Profenno’s, The Stockhouse Restaurant, Brea Lu, Baker’s Bench, or Paper City BBQ. Check out our new businesses too Owlbear’s Rest, Wakie Wakie’s and Sumo Sushi and Grill. Stop for a drink at The Daily Grind, Legend’s Rest Taproom, Westbrook On Tap, or Mast Landing Brewery for a beverage to keep you warm.
Gift cards make great gifts, too! Many of our downtown restaurants and businesses also have great swag – great for gift-giving!
