Winter Weekdays, Meetings Marketing, and Shoulder Season Marketing

We kicked off 2026 by showing off a different side of Greater Portland. Our winter campaigns leaned heavily into the region’s seasonal charm, inviting travelers to skip the summer crowds and experience the best of our coast during the quieter months of the year.

Winter Weekdays: Midweek Deals on Dining and Accommodations

Following its successful 2025 debut, our mid-week restaurant deal program, “Winter Wednesdays,” earned enough momentum to expand. This year, we evolved the campaign into “Winter Weekdays” by opening it Mondays – Fridays and inviting local hotels and accommodations to participate. This effort was proudly supported by the Maine Tourism Association, HospitalityMaine, the Maine Office of Tourism, Portland Downtown, and the Portland Regional Chamber of Commerce.

Campaign Promotion

Promoted through a strategic mix of paid Meta ads, organic social posts, food influencers, radio, email, and door-to-door outreach, ‘Winter Weekdays’ saw incredible community buy-in. In total, 80 restaurants and 32 lodging partners participated in the campaign.

Winter Weekday Website Analytics

Running from January 5 through April 30, the “Winter Weekdays” landing page drew impressive traffic and engagement. The site welcomed 7,600 unique users, generating 23,000 page views and 78,000 total interactions (clicks and scrolls).

January saw the highest traffic, with 12,000 views. The campaign achieved a strong 65% engagement rate, with visitors spending an average of 4 minutes and 45 seconds exploring the site.

Winter Weekdays in Consumer Newsletters

Our consumer newsletter reaches over 71,000 subscribers who have actively opted in to receive Greater Portland travel inspiration. These monthly emails feature regional updates, curated itineraries, and partner highlights. “Winter Weekdays” was featured in three of these newsletter campaigns, capitalizing on an audience that boasts an average open rate of 32%—well above the 20% industry standard.

Winter Weekdays in the news

The campaign gained media attention from outlets such as Boston.com, MaineBiz , WGME 13, Press Herald, and a segment featured participants on News Center Maine. Winter Weekdays was also featured on esteemed radio stations in both Boston and Maine.

Lynn Tillotson Interview with Celeste at 102.9 WBLM

Boston Radio Media Exposure Through Mix 104.1

Boston radio host Gregg Daniels (Mix 104.1) returned to Greater Portland with his family this past February as part of our ongoing media collaboration. Gregg shared his trip across his radio network and social channels, generating great buzz in the Boston market. His on-air spots introduced listeners to our local food and winter culture, while specifically driving traffic to the ‘Winter Weekdays’ campaign to inspire travel during our quieter months. View Instagram post here.

Mix 104.1 DJ Gregg Daniels Winter Weekdays Announcement on the air

Gregg Daniels’ Winter Weekdays mentions were featured across three Mix 104.1 segments, totaling 55 on-air mentions:

• Dirty on the 30 – weeks of 1/12, 2/9, 3/9 (15 mentions)
• Life in the Fast Lane – weeks of 1/12, 2/2, 3/2 (30 mentions)
• Mix Music Marathon – weeks of 3/16, 3/23 (10 mentions)

Audio clip from the week of 1/12/26

Featured businesses the Daniels’ family visited

Winter Weekdays Promotion Through Social Media

Supported by a mix of paid and organic social media, the campaign focused heavily on community alignment. We created a downloadable partner toolkit on the website, making it seamless for participating businesses to share matching content and amplify our reach. Furthermore, downloadable toolkit was created for the Winter Weekdays website, so our participating businesses could post aligned content of their own. View the toolkit here.

Our PR partner, Madden Media was posting paid campaigns on Meta on our behalf.

Analytics for Meta campaigns:

• Paid Facebook ads
  • 448,284 impressions 
  • 8,608 clicks
  • Click-through-rate of 1.92%
• Paid Instagram ads
  • 264,198 impressions
  • 6,444 clicks
  • Click-through-rate of 2.44%

Winter Weekday Food Influencers

This winter, we teamed up with several regional food influencers to get people excited about dining out mid-week. We hosted these creators at participating spots around town, and they did what they do best: shared incredible reels, stories, and reviews of their favorite winter dishes. By giving their followers an authentic, inside look at our local food scene, they generated a ton of buzz and reminded everyone that weekdays are a great time to grab a table in Greater Portland. From first to last picture: (@outofofficeenthusiasts, @eatingthroughtheseacoast, @travelikealocalma, and @themainefoodies on Instagram) Click the Instagram handle to view the posts.

Additional Winter marketing efforts

Madden Winter Campaign

To drive travel during the quieter months, we launched a targeted digital campaign using Google Search, programmatic advertising, and Meta remarketing. By focusing on winter events and local culture, we captured audiences actively looking to travel, effectively showcasing the region’s vibrant cold-weather appeal.

Campaign Performance

Clicks: 605K+

Impressions: 39.9M+

Winter Photographers

To give our winter campaigns a fresh look, we teamed up with three talented local and regional photographers to capture Greater Portland during its quietest months. They embraced the cold to photograph everything from crisp, snow-covered coastal views to the cozy, welcoming vibes inside our local shops and restaurants. Thanks to their hard work, we walked away with a greatly improved collection of authentic winter imagery that makes it easy to show travelers why Greater Portland is worth a visit all year long. Example of photography shots below. From L to R: (Mat Trogner shooting at Gritty McDuff’s Brew Pub with two friends, Andy Austin shooting at Saltwater Grille, Nicole Wolf shooting couple at Ri Ra Irish Pub).

List of Places That Were Included in Photoshoots

Winter Itinerary with Capshore Photography

To bring our winter marketing to life visually, we partnered with Amy Welch-Olson of Capshore Photography. A Maine native with a deep connection to the region, Amy has a gift for authentic storytelling that felt like a natural fit for this project. She then did what she does best, capturing real moments in real places. The result was a library of imagery that feels lived-in and genuine, along with a two-day winter itinerary written from firsthand experience. Read the itinerary here.

From midweek dining deals to Boston radio buzz to stunning new winter imagery, this season’s efforts were a true team effort — and it showed. With 80 restaurants, 32 lodging partners, and a whole community of local businesses, creators, and collaborators behind it, Winter Weekdays proved that Greater Portland doesn’t slow down when the temperatures drop. We’re already looking forward to building on this momentum and finding new ways to show travelers that there’s never a bad time to visit.

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