Looking Back at 2025—and Ahead to Holiday Happenings 2026

Holiday Happenings began with a straightforward idea: Salem already had the traditions, independent businesses, artists, events, and gathering places that make winter here feel special. What we needed was one place to find them—and a shared invitation to keep experiencing Salem after October.

Our first season became more than a calendar. It was a citywide story told through a tree lighting, local shopping, decorated windows, workshops, performances, tours, and many small moments in between.

A season that began together

The 2025 season took shape before the lights ever came on. The Johnson-Mitchell Family of Middleton donated Salem’s holiday tree, and Salem Main Streets and the City of Salem’s Department of Public Services helped bring it to Lappin Park and get it standing.

Then, on Friday, November 28, Salem gathered. Santa arrived atop the Hawthorne Hotel with the Salem Fire Department, and a lantern-lit procession made its way down Essex Street toward the tree. History Alive’s costumed carolers brought the music, Mayor Dominick Pangallo joined the celebration, and downtown filled with the kind of shared energy that makes a familiar tradition feel new again.

Small Business Saturday kept that momentum moving the next day. Dozens of downtown businesses participated with seasonal offers and experiences, giving residents and visitors a reason to wander, discover something unexpected, and put their holiday spending behind Salem’s independent businesses.

December brought the Holiday Window Decorating Contest and Wassail Weekend, with festive storefronts, roaming carolers, Santa visits, and another reason to spend time downtown. Across the full season, the Holiday Happenings calendar also gathered workshops, live performances, walking tours, museum programs, dining, local shopping, and creative experiences happening throughout Salem.

What made the first season work was not one event. It was the way Salem’s people, places, and traditions showed up together.

A better way to find winter in Salem

Holiday Happenings gave all of that activity a shared home. The calendar helped people plan a day or a weekend. The business directory made room for local shops, restaurants, attractions, venues, and organizations to tell more of their story. The blog introduced some of the makers, leaders, and community builders behind the season.

That visibility matters. It helps visitors find their way, gives residents a reason to rediscover downtown, and directs more attention toward the independent businesses and local organizations that keep Salem interesting all year.

For a first season, it gave us something even more important: a strong foundation to build on.

What we learned

The first year made a few things clear. People need to be able to tell the difference between an event they can attend and a holiday offer they can use. Businesses need an easy path to participate. Details need to be current, clear, and useful on a phone as well as a desktop. And the best way to invite someone into Salem is with specifics—not simply “shop local,” but whose shop, what experience, and why it is worth making part of the day.

That is why we have spent 2026 refining the Holiday Happenings website. Events and Holiday Deals now have separate homes. The calendar is easier to use. Business listings are more welcoming and easier to scan. Stories have more room to breathe. The goal is simple: make the site feel as thoughtful and distinctive as the people and places it represents.

The 2026 season starts here

We already have the first two dates on the calendar:

• Tree Lighting & Santa’s Arrival — Friday, November 27, 2026. Save the date and follow event updates.
• Small Business Saturday — Saturday, November 28, 2026. Save the date and follow event updates.

Dates for the 2026 Holiday Window Decorating Contest and Wassail Weekend will be announced as soon as they are confirmed. Event times, participating businesses, promotions, and full program details will be added throughout the fall. We will not fill the calendar with guesses; when information appears on the site, it should be something people can plan around.

Come build the next season with us

Holiday Happenings works because Salem shows up. If you are planning a visit, sign up for seasonal updates and start exploring the Events calendar and Business directory. If you represent a business, venue, artist, or community organization, see how to participate or support the season.

We are proud of what Salem built together in 2025. Now we get to make the 2026 season clearer, stronger, and even easier to experience.

Sources checked September 4, 2026: Salem Main Streets’ official records for Santa’s Arrival & Holiday Tree Lighting and Small Business Saturday.

Holiday Happenings is produced in partnership by Creative Collective and Salem Main Streets.