Boston Seaport Announces the Return of Community Drawing Series, Seaport Sketch, on May 5th
Draw Me Like One of Your Insiders, a New Live Portrait Series Featuring Local Artists, Launches for Seaport Insider VIPs in June
Boston Seaport by WS is bringing back its popular community art series, Seaport Sketch, and debuting a new Insider-exclusive experience, Draw Me Like One of Your Insiders, expanding its lineup of creative programming for the 2026 season.
Held every other Tuesday from May through November, Seaport Sketch invites participants of all ages and skill levels to channel their inner artist for complimentary, artist-led drawing sessions in The Superette Courtyard. In collaboration with SIDE Presents, the program is led by local artist Lee “SOEMS” and features rotating guest instructors. Each session offers a casual, inclusive environment with live music and guided exercises ranging from still life to live models and neighborhood-inspired subjects. All materials will be provided.
New this year, Draw Me Like One of Your Insiders gives Seaport Insider VIPs the opportunity to redeem points for a custom, hand-drawn portrait created by notable Boston-based artists, including Nick Shea and Rene James. Held every other Saturday from June through October at Harbor Way, the series highlights local talent while offering a unique rewards-based experience for Insider members.
WHEN:
Seaport Sketch
Every other Tuesday, May 5 – November 17, 2026
5:00 PM – 7:00 PM
View the artist schedule here.
Draw Me Like One of Your Insiders
Every other Saturday, June 6 – October 24, 2026
11:00 AM – 2:00 PM
Learn more here.
WHERE:
Seaport Sketch
The Superette Courtyard
131 Seaport Blvd, Boston, MA 02210
Draw Me Like One of Your Insiders
Harbor Way
Boston, MA 02210
*located between Ballers and Boston Provisions Market
ADMISSION:
Seaport Sketch: Free
Draw Me Like One of Your Insiders: 200 points redeemable through the Seaport Insider app.
*For Insiders who do not have 200 points available on the Insider app at the time of the event, simply connect a credit card to earn 200 points or stop by Splendoria, in The Superette Courtyard, and check in for points by scanning the QR code on-site.
SEAPORT INSIDER APP:
To become an Insider, download the Seaport Insider app and link a credit card. Insider VIPs earn perks from shopping at their favorite neighborhood retailers, attending events, and more.
Seaport Insider VIPs can earn points for attending Seaport Sketch via a QR code at check-in. The more points Insiders earn, the more rewards they can claim.
Guests can also use Insider points to redeem exclusive Seaport merch at class on select Seaport Sketch dates: May 5, June 30, July 28, August 25, September 22, and October 20.
Please see additional details on Seaport Insider here.
Credit: Boston Seaport by WS, Photographer Jason Cox
