GRAYSCALE Indie Business Summit Takes Over Downtown Salem

The GRAYSCALE indie business summit Salem has been waiting for finally has a date. From March 31 through April 2, downtown Salem transforms into a three-day hub for creative entrepreneurs. Specifically, it’s built for indie business owners, artists, and makers who have always felt like outsiders at traditional business events. Amber Newberry and the Die With Your Boots On team organized the summit to fill a gap the creative economy has needed to be filled for years.

Die with Your Boots On Co-owner and Grayscale Producer Amber Newberry

This isn’t another conference with corporate keynotes and name badges on lanyards. Instead, GRAYSCALE takes over Cinema Salem, the independent theater that has served as a cultural hub in downtown Salem since 2006. The summit delivers over 25 panels and Q&A sessions across both of its theaters. Additionally, there’s a dedicated small business expo, daily networking events, and after-hours gatherings at local businesses throughout the city. The setting itself reflects the spirit of the event — an indie theater, not a convention center.

What Is the GRAYSCALE Indie Business Summit?

GRAYSCALE is a conference built specifically for the people who make Main Street interesting. Think brick-and-mortar retailers, online shop owners, and in-person vendors. Also welcome are artists, influencers, content creators, boutique managers, and service providers. Essentially, it’s for anyone who does business a little differently.

Amber Newberry, founder of Die With Your Boots On and organizer of GRAYSCALE, put it directly: “The landscape of Main Street is changing. Let’s give it tattoos and a few piercings while we’re at it.”

That attitude runs through the entire event. After a tough 2025 for many small businesses, GRAYSCALE offers a much-needed reset. Consequently, attendees can expect fresh energy, honest conversations, and a community that truly understands indie business life.

What Panels and Sessions Can You Expect at GRAYSCALE?

The programming covers ground that most business conferences ignore entirely. Here’s a sampling of what to expect across the three days.

First, live selling and social commerce take center stage. “Fuck It, We’ll Do It Live” is a Q&A featuring FOXBLOOD and Die With Your Boots On on TikTok as a sales platform. Similarly, Lindsay Hearts of FOXBLOOD presents “Tipping the Scales.” That session addresses what happens when your business grows faster than you imagined.

Next, queer culture in business and marketing gets a dedicated panel. “Out of the Closet & Into the Media” features perspectives from Queer Videography, Geya Jenda, Ash Nunez of Old Growth Alchemy, and Miz Diamond Wigfall.

Then there’s tattoo entrepreneurship meets retail. “Tough Skin: Tattoo Meets Boutique” is a Q&A session with artists from Grim North Tattoo, Hemlock Tattoo, and Salem Ink.

Moreover, Main Street revitalization gets its own panel featuring Salem Main Streets, Creative Collective, Copper Dog Books, and The Castle. This session explores how modern Main Streets have evolved alongside Millennial and Gen Z consumers.

Furthermore, “Branding Without Compromise” tackles brand identity. Creators from Circle of Stitches, Trued Apparel, Notch Brewing, and Eternal October lead that conversation. Meanwhile, “The Salem Roundup” gathers owners of beloved downtown shops for a candid Q&A. Expect the owners of Die With Your Boots On, Witch City Wicks, Nocturne, and VampFangs/Velvet & Vein.

Additionally, the summit features sessions on photography in the age of algorithms, sustainability, accessibility, body positivity in marketing, and content creation strategy.

Where Does GRAYSCALE Take Place in Downtown Salem?

All panels, Q&A sessions, and keynotes happen at Cinema Salem, the independent four-screen theater inside the Witch City Mall. Its main entrance is on Church Street. Since opening in 2006, Cinema Salem has grown into one of downtown Salem’s most important cultural venues — home to the annual Salem Film Fest, live music, comedy, and community events alongside its regular film programming. For GRAYSCALE, both theaters run simultaneous programming each day.

Meanwhile, the small business expo runs daily at 10 Federal Street. That’s the office building directly across from Die With Your Boots On and Cinema Salem. The expo features resources, service providers, and small business organizations. It also includes a VRtical Media Immersion Lab. Drop-in attendance runs from 9:00 AM to 6:00 PM daily.

After hours, networking events take place at local Salem spots, including Notch Brewing and Legion. There will also be events along Church Street and at other downtown locations.

For those traveling to Salem, the organizers strongly recommend extending your stay. The weekend of April 3–4 brings additional community events. That Friday evening features the FOXBLOOD Sample Sale at 5:00 PM, followed by Vanta — a favorite local goth night.

How Much Are GRAYSCALE Tickets and How Do You Register?

Currently, three-day passes are available for $125. The organizers encourage purchasing the full pass to guarantee access to all programming. Registration is open now through the GRAYSCALE page at diewithyourbootson.com.

For sponsorship inquiries or general questions, contact Amber Newberry directly at amber@diewithyourbootson.com.

Who’s Behind GRAYSCALE? Meet the Sponsors and Organizers

GRAYSCALE is planned and organized by Amber Newberry and the Die With Your Boots On team. For those unfamiliar, Die With Your Boots On is a Salem-based indie retail brand on Church Street. It has championed independent culture since 2018.

The summit draws support from an impressive roster of local sponsors. Diamond sponsors are Creative Collective MA and Jenni Stuart Fine Jewelry. In addition, Obsidian-level support comes from Die With Your Boots On, VampFangs, Witch City Wicks, and FOXBLOOD. Onyx sponsors include Hive, Hemlock, Salem Uncovered, Laserbrain Patch Co./Grim North Tattoo, Nocturne, and Too Flame. Also on board are Jet sponsors VRtical Media and Love Letter Confections. Finally, event sponsors include Legion, Notch, and Creeping Death Designs.

As a Diamond Sponsor, Creative Collective is proud to support GRAYSCALE. It represents exactly the kind of community-building that strengthens the regional creative economy. When indie businesses connect and collaborate, everyone benefits.

Also worth noting: further sponsorship opportunities remain available for interested businesses.

Frequently Asked Questions About GRAYSCALE

Who is GRAYSCALE for?

GRAYSCALE welcomes indie business owners, artists, influencers, and content creators. It’s also for brick-and-mortar retailers, online shop owners, vendors, and service providers. In short, if you’ve ever felt like the odd one out at a business event, this summit was designed for you.

Is the schedule finalized?

The programming lineup is announced. However, specific times and listings may shift as the event approaches. Therefore, check the GRAYSCALE page at diewithyourbootson.com for the most current details.

Can I attend just one day?

Daily passes may be available. Nevertheless, the organizers recommend the three-day pass. This ensures access to everything across the full summit schedule.

Where should I park?

Cinema Salem is inside the Witch City Mall. Free parking is available in the Church Street lot after 6:00 PM. Alternatively, the mall parking garage works during the day. The expo at 10 Federal Street is a short walk from both venues.

I’m interested in speaking or being a panelist. How do I apply?

Simply contact Amber Newberry at amber@diewithyourbootson.com. Sponsorship opportunities are also available through the same contact.

This story comes from the Creative Collective community — Essex County businesses who believe that when we thrive together, our whole region becomes more vibrant. We’re entrepreneurs, creators, and service providers across all industries, collaborating to build the community we want to be part of. If you see your business as more than just commerce — as a way to contribute to our regional ecosystem — you belong here. Discover how to join our community →