Salem Main Streets: Downtown Revitalization & Community Events
If you’ve ever enjoyed the Salem Farmers’ Market on a Thursday evening in Derby Square, marveled at ice sculptures during Salem’s So Sweet, or received helpful directions from a smiling volunteer during October’s crowds, you’ve experienced the work of Salem Main Streets. This independent nonprofit has quietly transformed downtown Salem since 2001. Now co-organizing Holiday Happenings with Creative Collective, they’re bringing the same community-centered approach that made their other initiatives beloved Salem traditions.
From Vision to Reality: The Salem Main Streets Story
Founded in 2001 by the City of Salem in partnership with downtown businesses and residents, Salem Main Streets follows the National Main Street Four-Point Approach™—a proven strategy focusing on organization, promotion, economic restructuring, and design. When they launched, downtown Salem was almost entirely dependent on October tourism. Today, the city has become a year-round destination with thriving dining, diverse retail, and cultural programming through all four seasons—thanks in large part to Salem Main Streets’ work creating over 10,000-visitor events and providing crucial business support.
Leadership That Listens: Kylie Sullivan’s Vision
Since 2013, Executive Director Kylie Sullivan has guided Salem Main Streets with a leadership style that emphasizes community listening, strategic partnerships, and adaptive programming. Sullivan brought impressive credentials to the role—six years as a grants administrator at the Massachusetts Cultural Council, an M.B.A. from Simmons School of Management, and a B.A. in music from Wesleyan University—but it’s her genuine commitment to Salem’s downtown community that has defined her tenure.
“Our annual orientation will cover all the basics for new volunteers, and important updates and reminders for our returning ambassadors,” Sullivan explained about the organization’s extensive volunteer program. This attention to both welcoming newcomers and valuing returning supporters exemplifies her inclusive approach.
Under Sullivan’s direction, Salem Main Streets has consistently demonstrated the ability to adapt to changing community needs. During the COVID-19 pandemic, the organization quickly pivoted to provide crucial support to struggling downtown businesses, sharing resources about relief programs and adapting events to maintain community connection during challenging times. When businesses explicitly requested cohesive holiday marketing similar to Haunted Happenings, Sullivan and her team responded by partnering with Creative Collective to create Holiday Happenings.
Joining Sullivan is Assistant Director Elise Towle Snow, whose deep Salem roots—from A&J King Artisan Bakers to the Farmers’ Market—bring authentic community understanding. Her involvement with the Human Rights Coalition and Salem Public Schools’ LGBTQIA+ Action Committee reflects the organization’s commitment to truly inclusive programming.
The Thursday Ritual: Salem Farmers’ Market
Every Thursday from June through October, Derby Square transforms into Salem’s gathering place. The Salem Farmers’ Market, managed by Salem Main Streets since its relaunch, welcomes an average of 2,000 customers weekly who come for farm-fresh produce, artisan goods, live music, and the irreplaceable experience of connecting with their neighbors and the people who grow their food.
“We are so proud of our market vendors, and we hope to see many returning to us at Derby Square this season, but we’re also always on the look-out for the next up and coming business,” Sullivan noted. “This is the perfect opportunity for newer businesses looking to get to the next level, as well as established businesses looking to reach a new audience.”
The market’s location in historic Derby Square creates perfect synergy—the wide-open space accommodates vendors and allows for easy access from multiple directions, while the steps provide natural seating for those enjoying balloon artists or musical performances. Musical acts are sponsored by Creative Collective, demonstrating the ongoing partnership between the two organizations.
Beyond quality produce from farms like Clark Farm, Long Hill Orchard, and Wally’s Vegetables, the market creates genuine community connection. It accepts SNAP/EBT benefits ensuring access for all, hosts storytime for children, and turns the simple act of grocery shopping into an opportunity to strengthen neighborhood bonds. Dating back to 1634—with its peak around 1930 drawing 10,000 visitors on Saturdays—today’s market continues that centuries-old tradition.
Celebrating Creativity: Salem Arts Festival
Each June, downtown Salem transforms into a celebration of local creativity during the Salem Arts Festival, a collaborative production between Salem Main Streets and Creative Collective. Now in its 17th year, this free, family-friendly festival showcases local and regional artists through a juried gallery exhibition in Old Town Hall, outdoor performances across multiple stages, interactive art-making activities, a makers’ marketplace, live mural slam, and public art installations.
The festival draws over 10,000 attendees annually who come to experience everything from dance performances and live music to poetry readings and community art projects. Recent festivals have featured community projects like “Hissstory,” where participants created snake segments from upcycled materials, and have generated thousands of dollars in art sales—directly supporting local creators while attracting visitors to downtown businesses.
Winter Wonder: Salem’s So Sweet
When February arrives and winter weariness sets in, Salem Main Streets and the Salem Chamber of Commerce present Salem’s So Sweet Chocolate & Ice Sculpture Festival—now in its 24th year and one of the most popular winter events on the North Shore. This “decadent tradition of delectable chocolate, sparkling ice sculptures, and Valentine’s Day shopping” transforms downtown into a magical winter wonderland.
The festival kicks off with a Friday evening fundraiser at the PEM Connect Space where ticket holders receive commemorative glasses, complimentary wine pours, and goodie bags filled with sweet treats before embarking on a self-guided tour where participating businesses welcome them with wine tastings and delectable offerings. The real showstoppers are the 30 stunning ice sculptures strategically placed throughout downtown Salem—illuminated on Friday and Saturday evenings from 5:00 to 9:00 PM, weather permitting.
Past sculptures have included dragons, lobsters, Ruby Slippers from The Wizard of Oz, and the historic ship Friendship. Viewing the sculptures is free to all, ensuring this magical experience remains accessible to the entire community. The festival also features the “Chocolate Hearts Challenge,” an interactive game where participants search for special signage at participating businesses to win prizes.
Local businesses offer chocolate and Valentine-inspired specials throughout the festival weekend, creating opportunities for unique gift shopping while supporting downtown retailers during what is traditionally a slower season. Salem’s So Sweet perfectly exemplifies Salem Main Streets’ mission: creating experiences that drive foot traffic to downtown businesses, build community pride, and offer joy to residents during the darkest months of the year.
October’s Ambassadors: The Information Booth
Perhaps nowhere is Salem Main Streets’ commitment to community service more visible than at the October Information Booth, where over 100 volunteers assist more than 25,000 visitors during Salem’s busiest month. Stationed at the corner of Essex and Washington Streets, this booth becomes the welcoming face of Salem for tourists from around the world seeking directions, recommendations, and an understanding of Salem’s rich history beyond the witch trials.
Volunteers commit to a minimum of two-hour shifts after completing orientation training that covers everything from practical information about restrooms and parking to handling the most frequently asked questions: “Where can I see something really scary? Where did they burn the witches? Where can I get a good burger or fish meal?” (Answers: everywhere if you look closely at our history, they didn’t burn anyone in Salem—that was Europe, and Salem has excellent dining options throughout downtown.)
“If you enjoy helping visitors by showing them your enthusiasm for our cultured and historic city and want to make it fun and easy for visitors to explore all of Salem’s sites and attractions, please join us,” Salem Main Streets invites potential volunteers. The organization particularly seeks multilingual volunteers to assist the many international visitors who travel to Salem.
This massive volunteer effort represents a partnership between Salem Main Streets, the National Park Service, the City of Salem, Destination Salem, and the Salem Chamber of Commerce—but it’s Salem Main Streets that coordinates the training, scheduling, and management of this crucial resource. The booth ensures that Salem’s October visitors have positive experiences that encourage return visits during other seasons.
Beyond Events: Year-Round Business Support
While Salem Main Streets’ highly visible events garner well-deserved attention, the organization’s behind-the-scenes work supporting downtown businesses is equally crucial. Salem Main Streets provides direct and indirect business assistance, ranging from helping companies access resources and navigate city processes to connecting them with other organizations such as the Salem Chamber of Commerce, Destination Salem, and Creative Collective.
The organization serves as a liaison between businesses, facilitating collaboration on promotions, shared marketing efforts, and collective problem-solving. When businesses expressed frustration with scattered holiday marketing and requested cohesive strategies similar to Haunted Happenings, Salem Main Streets listened and responded by partnering with Creative Collective to launch Holiday Happenings.
Salem Main Streets also produces the annual Holiday Window Decorating Contest, encouraging downtown businesses to transform their storefronts into festive displays that enhance the shopping experience for residents and visitors. Award categories recognize creativity in different ways—from “Best Use of Products” to “Only in Salem” themes that highlight the city’s unique character. “We give the judges the freedom to create new award categories based on what they see each particular year,” Sullivan explained, ensuring the contest celebrates the diverse creativity of participating businesses.
The organization’s work follows the proven Main Street Four-Point Approach™: Organization (building leadership and cooperation in the business community), Promotion (creating a positive image for downtown), Design (improving appearance and ambiance), and Economic Restructuring (strengthening the economic base). This comprehensive approach addresses all aspects of downtown vitality rather than focusing narrowly on single issues.
The Power of 250 Volunteers
Salem Main Streets accomplishes its ambitious programming with a lean staff supported by an impressive volunteer base of over 250 community members who contribute thousands of hours annually. These volunteers do everything from setting up Farmers’ Market tents at 1:30 PM every Thursday to wrapping holiday ribbons on street poles on cold December mornings, from scooping ice cream at the Ice Scream Bowl to building signs for festivals.
The organization honors this volunteer commitment with an annual Volunteer Appreciation event where local restaurants donate food and the community comes together to celebrate those who give their time.
This volunteer network represents a true cross-section of the Salem community—longtime residents and recent transplants, young families and retirees, people fluent in multiple languages who can assist international visitors, and those with specialized skills who contribute expertise in areas from event production to graphic design. Many volunteers return year after year, creating continuity and institutional knowledge while mentoring newcomers.
The volunteer program also serves as an entry point for deeper community engagement. Many people volunteer at the October Information Booth and then discover other ways to contribute to downtown’s vitality. This ripple effect means Salem Main Streets not only accomplishes specific programmatic goals but also strengthens the overall fabric of civic participation in Salem.
Holiday Happenings: Partnership in Action
Salem Main Streets’ partnership with Creative Collective to co-organize Holiday Happenings represents the natural evolution of both organizations’ complementary strengths. Salem Main Streets brings established community credibility, municipal relationships, volunteer networks, and experience producing beloved free events like the Tree Lighting, Wassail Weekend, and Holiday Window Decorating Contest. Creative Collective contributes event production expertise, marketing prowess, and vendor relationship management.
Together, they’re creating exactly what the business community requested: cohesive holiday marketing that unifies multiple events under one strategic umbrella, similar to how Haunted Happenings successfully markets October. This partnership model—combining nonprofit community organizing with for-profit professional services—offers a sustainable approach to creating programming that serves businesses while keeping core community events free and accessible.
Salem Main Streets produces Holiday Happenings’ anchor community events:
Santa’s Arrival & Holiday Tree Lighting (November 29) brings thousands to Salem Common and Lappin Park for the magical moment when Santa arrives via Salem Fire Department ladder truck and the city’s holiday tree illuminates. History Alive performers lead caroling, and the event creates the perfect kickoff to Salem’s holiday season.
Wassail Weekend (December 14-15) encourages residents to shop local with special promotions, roaming carolers, and Santa appearances on Sunday. The event transforms downtown into a festive shopping destination during a crucial retail weekend.
Holiday Window Decorating Contest (starting December 7) showcases downtown businesses’ creativity with awards recognizing different approaches to holiday displays. The contest drives foot traffic as people stroll downtown to view competing windows and vote for favorites.
These events, combined with Holiday Happenings’ comprehensive business directory, event calendar, and marketing coordination, address the business community’s stated need for better-organized holiday promotion while maintaining Salem Main Streets’ core value of keeping community celebrations accessible to all.
Funding Salem’s Downtown Vitality
Salem Main Streets operates as an independent 501(c)(3) nonprofit, funded through the City of Salem, U.S. Department of Housing and Urban Development, Mass Growth Capital Corporation, Salem Chamber of Commerce, business sponsors, and individual donations. This independence allows nimble responses to community needs while maintaining strong partnerships with city government and Mayor Dominick Pangallo.
Support opportunities range from event sponsorships—Salem Arts Festival ($250-$5,000), Farmers’ Market ($175/week or $1,500/season)—to volunteer time. Tax-deductible contributions help Salem Main Streets continue keeping downtown vibrant, walkable, festive, and full of opportunity for locals, businesses, and visitors.
Why Salem Main Streets Matters
In an era when many American downtowns struggle with vacancy and online shopping competition, Salem’s downtown thrives. Salem Main Streets provides the connective tissue transforming individual businesses into a cohesive district—creating programming that gives people reasons to visit beyond transactions, maintaining physical and social infrastructure, and ensuring downtown’s voice is heard in city planning decisions.
Their work isn’t just about economic impact. It’s about creating shared experiences where neighbors meet, where residents develop city pride, where visiting families make memories, and where the social capital holding communities together gets strengthened. That doesn’t happen by accident—it happens because dedicated people at Salem Main Streets show up every day to do the often-invisible work of community building.
Connect with Salem Main Streets
Location: Derby Square, Salem
Phone:
Email: info@salemmainstreets.org
Website: salemmainstreets.org
Instagram: @salemmainstreets
Support through volunteering, sponsorship, or tax-deductible donations ensures this essential organization continues creating the events and community connections that make downtown Salem thrive.
About Holiday Happenings
Salem Main Streets is the co-organizer of Holiday Happenings, Salem’s comprehensive holiday events and business directory, in partnership with Creative Collective. Together, they’re creating the cohesive holiday marketing platform that Salem’s business community has been requesting—bringing together events like the Tree Lighting, Wassail Weekend, and Holiday Window Decorating Contest with enhanced business promotion and visitor resources.
Holiday Happenings is supported by Website Sponsors Jenni Stuart Fine Jewelry and Witch City Walking Tours, along with Social Media Sponsors Salem Wax/The Lost Library and Salem Night Tour/Wynott’s Wands. Learn more at salemholidayhappenings.org.
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