Merry Madness – Frequently Asked Questions For Businesses

The party starts at the U.S. Custom house on Fore Street!

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Whether you’re a seasoned participant or a newcomer, Merry Madness has undergone some significant changes, so let’s get everyone on the same page. We’ve compiled a list of frequently asked questions to help guide you. If you can’t find the answer you need, feel free to email our Marketing & Events Manager, McKenzie Delisle, at

Check out some FAQs below:


What is Merry Madness?

Merry Madness is a holiday shopping crawl. This ticketed event brings holiday shoppers together at the U.S. Custom House on Fore Street where they can enjoy some festive fun. As part of the package, they receive reusable shopping bags, wine/beer glasses, a pour of a beverage, a commemorative lanyard, and a map of participating businesses. Guests wear their lanyards and visit the participating stops — each offering an exclusive discount — shopping until they can shop no more!

When is 2023 Merry Madness?

Saturday, December 9, 2023 from 2 p.m. to 7 p.m.

How can my business participate in Merry Madness?

If you are a retailer, bar, or restaurant located in Portland’s downtown district, we encourage you to submit an exclusive offer for participating customers. Hotels, parking garages, and points of interest are also welcome to provide discounts on parking, overnight stays, and entry fees. Check out the map below to make sure you’re in the district!

NOTE: Offers must be submitted by November 1, 2023. Form available here.

When does my Merry Madness offer need to be active?

If you are offering discounts for retail, bars, or restaurants, they should be valid from 2 p.m. to 7 p.m. on the day of the event. However, discounts on overnight stays, parking, and entry fees are at your discretion. For instance, a hotel discount might be valid for the entire weekend (Friday to Sunday) or simply the night of the event.

How will I identify if a shopper is a Merry Madness participant?

To make our participants feel extra special, we will provide them with a branded lanyard to wear during the event. These shoppers will be easily identifiable, and we should ensure that any offers or deals are exclusive to them.

Is my business required to serve refreshments to participants during the event?

No. Although retailers previously provided refreshments to Merry Madness participants, this will not be the case in 2023. Instead, F&B spots will be partnering with us to offer Happy Hour deals during the event. If shoppers are interested in an eating and drinking experience, they can find details about the participating locations on their maps.

What is different about Merry Madness in 2023?

This year’s festivities are spreading beyond the Old Port! Portland Downtown has partnered with other organizations to offer activities across various downtown parks and locations, such as Congress Square Park, Monument Square, and Pleasant Street Park. The objective is to attract shoppers to different parts of downtown and to local businesses. If your business is located near one of these exciting areas, you won’t want to miss out on the fun!

Why is Merry Madness on a Saturday this year, instead of the usual Thursday?

After much thought, Portland Downtown staff made the tough call to switch things up with the regular Thursday night event. With the pandemic throwing a wrench in local businesses, it seemed like the smartest choice for everyone. But hey, if things take a turn for the better, we’re open to revisiting the decision in 2024.

What is Portland, Maine’s downtown district? 

It’s the geography Portland Downtown serves. It roughly stretches from Longfellow Square over to Franklin Street, with Cumberland Avenue as its northern boundary and the waterfront as its southern boundary. Here’s a map for a more detailed look!

What is Portland Downtown? 

Portland Downtown is a 501c4 nonprofit downtown improvement district funded through a supplemental tax paid by property owners within the district. Our mission is to stimulate a thriving, vibrant, and sustainable downtown community. 

Think of another question? Email Marketing & Events Manager, McKenzie Delisle, at