+ $4.20 taxes & fees
per person · $39.20 total
Since 1984, Trident Booksellers & Cafe have been a cornerstone of community in Boston’s Back Bay neighborhood. Owners Bernie and Gail Flynn came to the Boston area in 1983 from Vermont, where Bernie had also owned a bookstore. That store was started in 1976 at the end of the “hippie turned back-to-the-lander, turned Buddhist, turned entrepreneur” sort of era. Following the birth of their son, the Flynns moved to the Boston area in 1983 to raise a family. Recognizing the relative lack of spaces where one could linger over a book or a newspaper and drink a cup of coffee, they decided to incorporate a cafe to complement the bookstore. At the beginning, the future was uncertain, with little capital and a location then considered to be on the wrong end of Newbury Street. Now, decades later, both the bookstore and the cafe have grown from a small shop to a two-story business with a full menu ranging from traditional breakfast items (served all day), to fresh juices and smoothies, to comfort foods, and even beer and wine. And we’re always evolving. In recent years, we’ve expanded our catering and events programming. Now you can host a party in our upstairs dining room, or see a reading by up-and-coming authors. We’re opening our doors to you like never before.
Since 1984, Trident Booksellers & Cafe have been a cornerstone of community in Boston’s Back Bay neighborhood. Owners Bernie and Gail Flynn came to the Boston area in 1983 from Vermont, where Bernie had also owned a bookstore. That store was started in 1976 at the end of the “hippie turned back-to-the-lander, turned Buddhist, turned entrepreneur” sort of era. Following the birth of their son, the Flynns moved to the Boston area in 1983 to raise a family. Recognizing the relative lack of spaces where one could linger over a book or a newspaper and drink a cup of coffee, they decided to incorporate a cafe to complement the bookstore. At the beginning, the future was uncertain, with little capital and a location then considered to be on the wrong end of Newbury Street. Now, decades later, both the bookstore and the cafe have grown from a small shop to a two-story business with a full menu ranging from traditional breakfast items (served all day), to fresh juices and smoothies, to comfort foods, and even beer and wine. And we’re always evolving. In recent years, we’ve expanded our catering and events programming. Now you can host a party in our upstairs dining room, or see a reading by up-and-coming authors. We’re opening our doors to you like never before.
Since 1984, Trident Booksellers & Cafe have been a cornerstone of community in Boston’s Back Bay neighborhood. Owners Bernie and Gail Flynn came to the Boston area in 1983 from Vermont, where Bernie had also owned a bookstore. That store was started in 1976 at the end of the “hippie turned back-to-the-lander, turned Buddhist, turned entrepreneur” sort of era. Following the birth of their son, the Flynns moved to the Boston area in 1983 to raise a family. Recognizing the relative lack of spaces where one could linger over a book or a newspaper and drink a cup of coffee, they decided to incorporate a cafe to complement the bookstore. At the beginning, the future was uncertain, with little capital and a location then considered to be on the wrong end of Newbury Street. Now, decades later, both the bookstore and the cafe have grown from a small shop to a two-story business with a full menu ranging from traditional breakfast items (served all day), to fresh juices and smoothies, to comfort foods, and even beer and wine. And we’re always evolving. In recent years, we’ve expanded our catering and events programming. Now you can host a party in our upstairs dining room, or see a reading by up-and-coming authors. We’re opening our doors to you like never before.
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Jenny wears the paint as often as she paints with it. She believes in having fun and getting messy, especially when it comes to art. Her favorite part of teaching is getting to hear and tell stories while the paint is flying about. Come discover the creative side you never knew you had!
Questions about what to expect, what’s included, and how it all works.
Yes. Cardinal's Winter Paradise is designed to be achievable at any experience level. More satisfying than it looks difficult — Jenny breaks every step down clearly. Most of our guests have never picked up a brush before, and they leave with something they're genuinely proud of. Worth knowing: Paint Nite events happen at real bars and restaurants, not studios — it's a night out that happens to involve painting.
A painting class teaches you technique. Paint Nite gives you a finished painting and a good night. Jenny is a real local artist — not a teacher running a curriculum — and this event happens at Trident Booksellers & Cafe, a real local spot, not a studio. Paint Nite invented this format in 2012 and has sold more than 10 million tickets. The trade-off is honest: lighting varies, it can get loud, and the person at the next easel is a stranger. That's the point. It's more of a night out than a class.
Jenny is a real local artist based in Boston — not a franchise employee or a corporate hire. In Boston, 5 out of 9 Paint Nite guests rated their instructor as amazing. Jace C. said: 'So much fun, they were so helpful and made the night exciting'
Trident Booksellers & Cafe is a local venue in Boston — a real local spot, not a dedicated painting studio. Paint Nite events happen at places like this by design — venues with character, regulars, and a bar. It can get lively. That's what makes it a night out rather than a class.
Yes — we have 47 upcoming events in Boston this month. You can view them here.
Cardinal's Winter Paradise is a winter painting — cozy seasonal vibes for a great night out.
Yaymaker is Paint Nite. We brought both brands together under the Paint Nite name — same artists, same events, same format we invented in 2012. More than 10 million tickets have been sold across both brands combined. If you used to attend Yaymaker events in Boston, you're in the right place. Welcome back.
Your ticket to Cardinal's Winter Paradise includes the canvas, all the paint you'll need, the use of brushes and an apron during the event, and step-by-step instruction from Jenny . Drinks and food are ordered separately from Trident Booksellers & Cafe — you pay the venue directly for anything you eat or drink.
Trident Booksellers & Cafe's event starts at 7:00 PM. We suggest showing up by 6:30 PM to give yourself time to pick your seats, get a drink and maybe a bite before Jenny starts the painting.
You can reschedule your ticket to any other Paint Nite event up to 24 hours before this one starts. After that, tickets are locked — no refunds or changes. If Paint Nite cancels this event for any reason, you'll receive a full automatic refund.
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