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Merry Madness Shopping Tour
Shop local and win prizes across 60+ downtown businesses.
About
Get ready for Merry Madness, Portland's festive two-week shopping tour! From November 29 to December 15, explore over 60 downtown businesses, collect stickers, and enter to win fantastic prizes, including a stay at The Westin Portland Harborview. Don't miss Locals Night on December 12 for exclusive wine and festive fun.
Our Take
Family Friendly
Best For
Holiday shopping, supporting local businesses, prize seekers
Vibe
Festive, community-oriented, shopping-focused
Energy Level
Moderate
Budget
$
Photo Friendly
Weather Sensitivity
Low
Special Events & Promotions
- Collect stickers from participating businesses to enter prize drawings.
- Grand prize includes a two-night stay at The Westin Portland Harborview.
- Locals Night on December 12 with exclusive wine and a limited-edition glass.
- Offers valid from November 29 to December 15.
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.
Location
Event Details
Pricing
$
Duration
Two weeks
Ages
Everyone
Neighborhood
Downtown Portland
Timed Entry
No
Organizer
Portland Downtown
Practical Information
Parking
Information on affordable parking options is available from the City of Portland Parking Division.
Pet Policy
Not specified
Food & Drink
Exclusive Merry Madness wine available at select locations during Locals Night.
Quick Actions
Tips & Advice
- Plan your route in advance using the online offers sheet to maximize your shopping experience and sticker collection.
- Check the hours of individual participating businesses, as they may vary from standard operating times.
- Consider using public transportation or walking to navigate downtown Portland easily and avoid parking hassles.
- Take photos of your collected stickers and email them to info@portlandmaine.com to ensure your entry into the prize drawings.
- On Locals Night (December 12), arrive early to select locations to secure a limited-edition wine glass with your Merry Madness wine.
Frequently Asked Questions
How do I get a shopping map?
You can pick up your shopping map at the Monument Square Tree Lighting event on November 29, or at any participating business during the tour.
How do I enter the prize drawings?
Collect at least three stickers from participating businesses for a chance to win. Gather 10 stickers from 10 different stores for the grand prize drawing. Email a photo of your stickers to info@portlandmaine.com with 'Merry Madness Prize Entry' in the subject line.
What are the dates for Merry Madness?
The event runs from Friday, November 29, to Sunday, December 15.
Is there a special event for locals?
Yes, Merry Madness Locals Night is on Thursday, December 12, from 4:00 to 7:00 p.m., featuring exclusive wine from Blue Lobster Urban Winery at select locations.
Are there any transportation recommendations?
Information on multi-modal transportation options for getting around downtown Portland and affordable parking is available on their website.
