Rollin’ into Boxboro MA, Ian Stuart is a Comedian, Writer, Director, Actor

Rollin' into Boxborough MA, Ian Stuart is Comedian, Writer, Director, Actor

Ian Stuart is a stand-up comedian and writer from Portland, Maine. Ian is the founder of The Portland Maine Comedy Festival and The Maine Comedy All-Stars. Ian is the head writer for the Maine Cannabis Chronicle and writes, directs, and co-stars as “Mark” in the popular web series “Welcome to Maine“. As a stand-up comedian, he is known for his vivid storytelling, sharp one-liners, and playful crowd work. Ian has been featured at many of the theater and concert venues in New England, opening for the likes of Dave Attell, Jay Mohr, Maria Bamford, Demetri Martin, and many more. From rowdy late-night club shows to clean corporate comedy, Ian can please any comedy crowd.


Ian Stuart is a funny guy. He thinks maybe he was born that way since he has been interested in comedy for as long as he can remember. As a kid, he says he had every Farside and Calvin and Hobbes book ever released. He was also obsessed with Mel Brooks and Monty Python films and got a taste for performing when he auditioned for a play in junior high because it had a scene from The Holy Grail. The first albums he bought with his own money were John Pinette’s “Show me the Buffet” and Chris Rock’s “Born Suspect.” Now he has released a comedy album of his own called “Day Drinker” on Acuity Records.

Stuart is hoping that his mother is not going to read this, but while in high school, he snuck into the Comedy Connection to watch local comedians try out the material. “Senior year, I occasionally performed at bars I shouldn’t have legally been in,” he said.

After graduating from GHS, Stuart attended Franklin Pierce College in New Hampshire, majoring in business, but the entertainment was never far from his thoughts. He performed occasionally at the Comedy Connection in Portland while completing his degree and then worked in group homes after college, before deciding to pursue comedy full-time.

Stuart has performed all over New England and Canada, at colleges and comedy venues in Chicago, Texas, Ohio, and New Mexico. He loves traveling and he loves making people laugh, adding, “I like to give people a temporary distraction from a long work week.”

To Stewart, comedians are storytellers and he honed his skills hanging around a campfire with family and friends as a kid. He believes that being from Maine has definitely put a stamp on his style of comedy. “People from Maine have a natural wit and a talent for storytelling, it’s hard to find someone from Maine that doesn’t have a funny story to tell,” he said. Stuart is constantly working to perfect his craft, seeking help and feedback from many of the comedians who perform in the area. “If you ask questions and are interested in the response, you’ll get help from everyone,” he said.


About the show

October 7-9, 2022
The Boxboro Regency Hotel and Conference Center, Boxborough, MA
Tickets are available now!

You must be at least 21 years of age to enter the private property.

The HighLifeStyle Show

There will be over 30,000 sq ft indoor and outdoor gathering of brands, dispensaries, distributors, growers, artists, performers, and consumers to converge in the HighLifeStyle of B2B and B2C in a resort hotel conference setting with exhibitors, vendors, concerts, comedy, education, celebrities, socializing and networking.

Offering exhibitors and vendors a fun environment to meet qualified customers who are interested in canna-related products, services, and creative arts.

As a business conference, one of The HighLifeStyle Show’s goals is to have businesses, entrepreneurs, and brands will be able to meet the distributors, retailers, and consumers in an entertaining, safe environment. Retail distributors can promote their products and retail locations in order to compete to attract new customers. Artists can find new fans. Craft growers can network to find supplies they may need to be an at-home botanist, or find outlets or job opportunities.

As a LifeStyle conference, we will be showcasing all aspects of the canna-inspired culture including health, wellness, music, art, clothing, literature, food, cultivation, supplies, medical, educational, and ancillary aspects including cannabis weddings and travel.

There will be two levels of participation involving access to indoor and outdoor activities. All attendees will be able to access all of the Exhibitors indoors and out.

Live Music On The Main Stage Outdoors All Weekend Long Includes
The Wailers, Roots of Creation, Jon Butcher Axis, Brett Wilson, Mikaela Davis, Barrence Whitfield, Walter Sickert & The Army of Broken Toys, Tsunami of Sound, Justine’s Black Threads, and more.

Laugh your bud off with LIVE Comedy & Stand-up
Starring Matt Barry, Mona Forgione, Ian Stuart, and Josh Day will be performing standup comedy, all weekend long.

Click Here For more info on Exhibitor Space or Sponsorship, or email: or

About the Venue

Boxboro Regency Hotel (978) 263-8701 Located in a rural area near several corporate offices, this conference hotel is 1 mi (1.6 km) from I- 95 and within 1 mi (2 km) of Oxbow National Wildlife Refuge. A 20-minute drive from downtown Boston. The warm, traditionally furnished rooms feature free Wi-Fi access, a flat-screen TV, a coffee maker, and a seating area. Higher classrooms have mini-fridges and/or a balcony or terrace overlooking the pool. Suites also include sofa beds and microwaves, while higher-end suites have separate living rooms. The on-site full-service restaurant is open for breakfast, lunch, and dinner and serves modern American fare. Guests can unwind on the indoor pool deck. Additional amenities include an exercise facility and an indoor pool. The hotel provides free parking and is pet friendly.

While there are many pleasant restaurants close to our hotel, we are happy to offer guests delicious on-site dining options. Enjoy breakfast, lunch or dinner at our casual restaurant Minuteman Grille American Pub. You can also enjoy a delicious meal served directly in your room.

Amenities consist of a tropical atrium with a fountain, free Wi-Fi, free parking, disabled access, an indoor pool, restaurant, bar, room service, and air conditioning. Refrigeration, Airport Shuttle, Pets Allowed, Dogs Allowed (please call hotel for more information 978-263-8701). In addition, for hotel guests, we provide a fully equipped fitness center that includes changing rooms and showers, treadmills, ellipticals, stationary bikes, and free weights. Stay in control of your business with our on-site business center, which offers computer, printer, and fax services.

Rollin’ into Boxborough MA, Ian Stuart is Comedian, Writer, Director, Actor