Portland’s Downtown District Events
PDD produces many events throughout the year, here is a list of our cornerstone events that are not to be missed! For a full listing of Portland events, visit our events page.
39th Annual Old Port Festival – Sunday, June 10, 11am – 5pm
Celebrate the beginning of summer in beautiful downtown Portland with multiple music stages, Maine-made arts and crafts, and food from local businesses, kid’s activities, and more! The festival begins at 11am with a foot powered parade down Exchange Street led by the Shoestring Theater!
Alive at Five FREE Concert Series – Monument Square- Thursdays, July 12 – August 9, 5pm – 7:30pm
Kick back, enjoy free music by your favorite bands in the summer sun, and enjoy a cold drink in the beer garden
Weekday Performance Series – Tuesdays, Noon – 1pm
Post Office Park – July, 10, 17, 24, 31
Congress Square – August 7, 14
See a fun lunchtime performance from local jugglers, magicians, and other entertainers!
Weekday Music Series – Fridays, Noon -1pm
Post Office Park, July 13, 20, 27
Congress Square, August 3, 10, 17
Take a break from your busy work day to hear music from up-and-coming local bands!
Kids Activity Day
Lobsterman’s Park, 10:30am -11:30am
Wednesdays, July 11, 18, 25, Aug 1
A new activity every week presented by the Children’s Museum & Theatre of Maine.
Annual Christmas Tree Lighting – Friday November 23, 5:30pm, Monument Square
Come see the spectacular lighting of the tree at this annual tradition! Entertainment begins with Rick Charette and the Bubblegum Band.
Twelve Days of Christmas – Friday November 23 – Sunday December 16
Every weekend during the holiday season, downtown merchants
Horse & Wagon Rides – Saturday and Sunday November 24 to December 23- Saturdays (2-6pm) and Sundays (1-5pm) Free rides on a horse drawn carriage throughout enchanting downtown. Enjoy the lights and sounds of the holiday season. Pick up and drop off every half hour in Monument Square.
Shop For A Cause Day – Saturday December 1 - Shop downtown on December 1 and a portion of the sales from participating stores are donated to a local charity.
Think Outside The Box- Saturday December 8 – Shop the Arts District and discover demonstrations, holiday sales, live music, family activities, and more!
Merry Madness – Thursday December 13, 5-10pm – Shop ‘til you drop in downtown Portland! Participating stores will remain open until 10 pm. Merry Madness kicks off downtown with music, food, and fun! It’s a night full of fun with your friends- shop, eat, and be merry!
Winter Window Walk – Stroll through downtown during the holidays to enjoy the festive window displays! Vote for your favorite by emailing info@portlandmaine.com by December 16.
Holiday Light Sculptures – Experience our radiant holiday light sculptures by artist Pandora LaCasse – Portland’s signature holiday decoration.
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