Merry Madness

Join us for the Merry Madness Shopping Tour! This festive two-week shopping extravaganza is your chance to explore local businesses and win exciting prizes!

Plan your 2024 shopping route!

Explore offers at more than 60 participating downtown businesses. Offers Valid Nov 29, 2024 – Dec. 15, 2024.

Explore the Offers

It’s almost that time of year!

Embark on a delightful shopping adventure from November 29 to December 15! Collect stickers as you shop at participating businesses in downtown Portland. One sticker per customer, per store. Visit at least 10 businesses to enter our grand prize drawing for a two-night stay at The Westin Portland Harborview!

Dates: Friday, November 29 – Sunday, December 15
Note: Business hours may vary, so check with individual stores!

Everyone is welcome! No ticket is required. Pick up your shopping map at the Tree Lighting event in Monument Square on November 29 (look for the blue Portland Downtown tent!) or at any participating business during the tour.

To enter our fabulous prize drawing, collect at least three stickers by shopping at three participating businesses. For the grand prize, gather 10 stickers from 10 different stores! Snap a photo of your stickers and email it to info@portlandmaine.com with “Merry Madness Prize Entry” in the subject line.

Click here for information on multi-modal ways to get around downtown and here for affordable parking options from the City of Portland Parking Division.

Merry Madness Locals Night

Thursday, December 12, 2024

Join us for a special evening of local shopping and festive fun! From 4:00 to 7:00 p.m., enjoy exclusive Merry Madness wine from Blue Lobster Urban Winery at select locations:

Order a glass of Merry Madness wine and receive a limited-edition wine glass (while supplies last). Dress up, shop local, and support your community!

Let the holiday shopping fun begin!

Click here for a list of participating businesses and map out your route!

Presented by Hood® Eggnog! Thank you to our sponsors:

2023 Recap

The 2023 festivities started off with a bang at Portland’s historic U.S. Custom House in the lively Old Port District! Shoppers were treated to their beverage of choice and other delightful goodies before using their printed map to find discounts at more than 70 spots participating locations.

Become a Merry Madness Business!

Learn how to join the madness as a participating business.

Become a Merry Madness Sponsor!

Are you interested in becoming a sponsor for a Portland Downtown event or another exciting program? We’d love to hear from you! Email us at info@portlandmaine.com with “Sponsor Interest” in the subject line. Share your business or organization’s sponsorship goals, and we’ll help match you with the perfect event or program!

Why Sponsor with Us?

Boost Your Brand: Increase visibility and showcase your commitment to the community.

Connect Locally: Build relationships with local businesses, residents, and visitors.

Support Growth: Help fund projects that stimulate a thriving downtown environment.

Gain Recognition: Receive acknowledgment through our marketing channels, event promotions, and more.

Ready to Get Started?

Fill out the form below to express your interest in becoming a sponsor. Once submitted, a member of our team will get in touch with you to discuss available opportunities and how we can best align your support with our community needs.