President’s & CEO’s Update – October 2026
October brings a noticeable change of pace to Greater Cape Ann as we move from the busy
summer season into fall. While the crowds and rhythms may shift, there is still plenty
happening throughout our communities. Our downtown Gloucester Visitor Center will
remain open on weekends through the end of October, helping visitors discover local
businesses, attractions, events, and all that Greater Cape Ann has to offer during this
beautiful time of year. The Chamber’s calendar is just as active, with opportunities to
connect our business community, bring visitors to the region, and celebrate some of the
traditions that make the fall season so special.
Before looking ahead, September was an incredibly productive month. We kicked things off
with our third and final Gloucester Main Street Block Party on September 4. After a
successful summer series, it was a great way to close out another season of bringing
residents and visitors downtown for live entertainment, dining, shopping, and community
fun.
September also provided several opportunities for our members to connect. Our Business
After Hours at the Essex Historical Society & Shipbuilding Museum offered a wonderful
setting for networking while showcasing an important part of Essex’s history. Later in the
month, the Businesswomen’s Golf Outing at Rockport Golf Club brought together golfers of
all skill levels for an afternoon of fun, networking, and camaraderie. We are grateful to our
hosts, committees, and everyone who participated in both events.
The Chamber’s 39
th Annual Auction on September 24 was another tremendous success.
This year’s Together, Let’s Glow theme brought a fun and welcoming energy to Cruiseport
Gloucester, and our guests enthusiastically embraced the evening. As the Chamber’s
largest annual fundraiser, its success provides important support for the programs, events,
advocacy, and initiatives we deliver throughout the year. A heartfelt thank you to all of our
donors, bidders, sponsors, attendees, volunteers, and Auction Committee for making the
evening possible, and a special thank you to Al Temkin Productions for serving as our
auctioneer and emcee and helping keep the evening moving and entertaining.
We closed the month with two programs focused on the future of our communities. The
Downtown Essex Visioning Forum brought businesses, residents, and community leaders
together to review survey results and discuss shared priorities for the town center. The
following evening, our Greater Cape Ann College & Career Fair at Ipswich High School
brought together more than 60 colleges and universities, over 20 businesses, and a strong
turnout of students and families exploring opportunities beyond high school.
Looking ahead, October offers several opportunities for members to connect with one
another. We begin with the Ipswich Business Meet-Up on Wednesday, October 7 at Ipswich
Country Club, bringing Ipswich businesses together to strengthen connections and
continue conversations about supporting the local business community. On Wednesday,
October 14, members can start their day with Coffee & Connections from 8:00 to 9:00 a.m.
at the Chamber, sponsored by MassHire. Later in the month, Cape Ann Savings Financial
Advisors will host our Business After Hours on Wednesday, October 21, from 5:00 to 7:00
p.m. Whether you prefer morning coffee or an evening gathering, we hope you’ll take
advantage of one or more of these opportunities to make new connections and strengthen
existing ones.
October also brings two of our favorite fall community traditions. On Saturday, October 17,
downtown Rockport will come alive for Rockport Harvest Fest, featuring vendors
throughout downtown, beer and food trucks, entertainment, and the always-popular Apple
Pie Bake-Off. We’re still looking for bakers to put their best pie forward for a chance to earn
the bragging rights of having one of Greater Cape Ann’s best apple pies! Harvest Fest is an
important shoulder-season event, giving residents and visitors another reason to explore
Rockport, shop locally, and support area businesses beyond the summer months.
Then on Saturday, October 24, we look forward to another beloved Greater Cape Ann
tradition with Essex ClamFest. This year’s event will feature eight chowder competitors,
including some new contestants joining the competition, along with food, live music, and
more than 40 vendors. Celebrating Essex’s rich clamming and culinary heritage, ClamFest
brings residents and visitors together for a quintessential New England fall experience and
an important day for businesses throughout the community.
We’ll close out a very busy October with the $20K Game on Wednesday, October 28 at The
Cut. Tickets are still available for $100 each, and every ticket provides a chance to win the
$10,000 grand prize. This popular Chamber fundraiser is always an exciting evening, and
we encourage members to get their tickets while they’re still available and join us for the
drawing.
October is a great example of the breadth of the Chamber’s work. From convening
businesses and creating networking opportunities to producing community events that
drive visitation and supporting conversations about the future of our downtowns, each of
these efforts contributes to stronger businesses and stronger communities. There are
plenty of opportunities to get involved, participate, and connect over the next month and a
half, and we hope to see you at one, several, or all of the events ahead. Whether you join us
for networking, support one of our community events, participate in a Chamber program,
or simply stop by to say hello, your involvement is what makes these efforts successful.
As always, thank you for your continued participation, partnership, and support. We look
forward to a busy and exciting fall together.
Warmly,
Keith Harris, President, GCACC Board of Directors
Sam Bevins, CEO, Greater Cape Ann Chamber of Commerce