Salem Celebrates the Season with Holiday Happenings 2026

GUEST BLOG | Written by John Andrews, Creative Collective, and Kylie Sullivan, Salem Main Streets

Holiday Happenings 2026 is presented by Jenni Stuart Fine Jewelry and Blackcraft Salem. Some businesses featured below support the campaign through sponsorships or paid directory listings.

Salem, Massachusetts, celebrates the holidays through the people who make this city their own: shopkeepers, artists, performers, neighbors, and the families who return to the same traditions each year. From Friday, November 27, through Thursday, December 31, 2026, Holiday Happenings brings downtown’s signature celebrations together with local shopping, performances, and winter experiences.

Through our partnership between Creative Collective and Salem Main Streets, we’re gathering the season at SalemHolidayHappenings.org. The invitation is simple: spend time in Salem, reconnect with a favorite place, and get to know someone doing something wonderful a few doors down.

Kylie Sullivan, executive director of Salem Main Streets, describes the community behind the season:

“From free events open to anyone, to festive decorations hung by resident volunteers and city employees, windows designed by businesses to make the downtown brighter, and of course, elevated initiatives like our joint Holiday Happenings campaign with Creative Collective promoting the incredible range of local commerce and events, everything is intentionally focused on this community and the people in it.”

A season that starts with everyone looking up

On Friday, November 27, the place to be is Salem Common. Arrive by 5:45 p.m. and look toward the Hawthorne Hotel, where Santa appears at 6:00 p.m., with help from the Salem Fire Department.

Then the celebration moves through downtown. A procession follows the Essex Street Pedestrian Mall to Lappin Park, beside the Bewitched statue, where we’ll join Santa, Mayor Dominick Pangallo, and period carolers from History Alive for Salem’s Holiday Tree Lighting. Salem Main Streets and the City of Salem bring these two traditions together in one evening.

There’s something especially fitting about beginning the season with a walk together. The Common, Essex Street, and Lappin Park become part of the same celebration. Whether this is a family tradition or a first visit, there’s a place in the procession.

The people behind a Salem gift

Small Business Saturday follows on Saturday, November 28. It’s a good day to turn a familiar corner, step inside a shop you’ve been meaning to visit, and ask the person behind the counter what they’re making or loving this season.

At Jenni Stuart Fine Jewelry on Front Street, the work is designed and made in Salem by a goldsmith-owned studio. On Essex Street, Witch City Wicks tells another local story: Liz Frazier began the business at home in 2011, and its Salem team now pours and labels candles in-house.

A few blocks can hold very different expressions of the same city. Nocturne on Front Street brings together dark romantic design and work by independent artists. Blackcraft Salem on Essex Street pairs its distinctive shop with Blackcraft Coffee inside, so browsing can turn into a coffee break without leaving the building.

That variety is part of what we’re celebrating. A gift can be beautiful, useful, funny, a little strange, or something made by the person handing it to you. The Holiday Happenings business directory is a starting point for finding the shops, restaurants, and experiences that give Salem its range.

Storefronts become part of the celebration

From Friday, December 4, through Tuesday, December 29, the Holiday Window Contest gives downtown businesses another way to show their creativity. Salem Main Streets selects judges, and the displays give everyone else a reason to take the long way down the street. The 2026 participant list is to be announced; check the contest page as December 4 approaches.

Make an evening of the windows with a friend. Stop for dinner, compare favorites, and look closely at the details someone has spent time arranging. A storefront becomes a small contribution to a much larger downtown celebration.

Salem’s seasonal imagination also reaches inside its attractions. At Salem Wax, Ghosts of Holidays Past draws on Victorian holiday storytelling. Check the museum’s current seasonal information for its Holiday Glow experience and other offerings.

A weekend to enjoy our downtown

Wassail Weekend returns Saturday and Sunday, December 12–13. Salem Main Streets created the initiative to encourage residents to shop locally and enjoy downtown during the holiday season.

We like that starting point. Make time for brunch, browse without rushing, and leave room for a stop you hadn’t planned. It’s an invitation to enjoy the places that are part of everyday Salem, with the season giving us another reason to gather.

The 2026 participating-business lineup and detailed schedule are to be announced. Check the Wassail Weekend page as plans are confirmed; individual businesses set their own hours.

Count down together at Charlotte Forten Park

The season closes with New Year’s Eve LAUNCH! on Thursday, December 31, from 5:00–6:00 p.m. at Charlotte Forten Park, 289 Derby Street. Salem Main Streets and the City of Salem host the family-friendly celebration, with an early countdown just before 6:00 p.m.

It’s a chance to welcome 2027 in the company of the city, with time afterward for dinner, another celebration, or getting small children home. Admission information and additional program details are to be announced.

Keep a little time for Salem

A big event can bring us downtown. So can a candle, a conversation, a beautifully arranged window, or the promise of coffee with someone we haven’t seen in a while. Holiday Happenings connects those moments across the season.

We hope you’ll join us for a tradition you love and make room for a new one. Start with the Holiday Happenings events calendar, check the organizer’s latest details, and choose a day to spend with Salem.

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