The New England Cigar Expo 2026

On September 25 and 26, hundreds of cigar enthusiasts descended on Dreamers’ Ranch in Windham, New Hampshire, for an event that has become increasingly difficult to define by traditional cigar-festival standards. Organized by Dave Garofalo and the team at Two Guys Cigars, the 2026 New England Cigar Expo was part cigar gathering, part dinner, part comedy show, part game show, part competitive-eating spectacle, and, ultimately, a two-day celebration of the people and culture surrounding premium tobacco.

This year, Mother Nature added her own entertainment. A powerful late-September nor’easter moved into New England during the weekend, bringing heavy rain, strong winds, and widespread disruption throughout the region. Yet the weather did little to diminish the enthusiasm at Dreamers’ Ranch. Guests arrived from across the United States and as far away as Kuwait, Canada, and Scotland, determined not to miss an event with a reputation unlike anything else in the cigar world: a choreographed weekend of cigar culture and live entertainment.

Each guest received 32 cigars with the 2-day pass or 16 cigars with the Saturday-only 1-day pass. VIP ticket holders also had access to early entry and goodies, including an after-hours event where they attended a live broadcast of The Cigar Authority podcast.

Friday evening began with VIP access at 5 p.m., followed by a cocktail hour and dinner. Roughly 400 guests eventually filled the property for the evening's festivities. The setting was relaxed but unmistakably celebratory. A professional DJ provided the soundtrack while cigar enthusiasts gathered with friends, manufacturers, and industry personalities. 

Sixteen cigar companies represented some of the most recognizable names in premium tobacco together in one location. Among them were Nick Perdomo of Perdomo Cigars, Nestor Miranda of Nestor Miranda Cigars, Steve Saka of Dunbarton Tobacco & Trust, Eric Newman of J.C. Newman Cigar Co., Rafael Nodal of Aging Room, Christian Eiroa of CLE Cigars, and Glen Case of Kristoff Cigars.

At 7 p.m., cocktails gave way to a multi-course sit-down dinner featuring roast prime rib. As guests ate, Garofalo moved through the room, playing one of his trademark games and offering $50 or $100 to lucky winners. Boston-area comedian Lenny Clarke continued the entertainment with a stand-up performance after dinner. Then came the event's centerpiece, the game show that gave away $25,000 in cash. The atmosphere changed immediately, from a cigar dinner to a competition, with guests watching, laughing, shouting, and hoping they might walk away with the grand prize.

Friday night also provided one of the weekend's most meaningful moments. The Cigar Hall of Fame induction ceremony recognized Montecristo Cigars, officially adding one of the world's most recognizable cigar names to the Hall's growing history. Rafael Nodal accepted the honor on the brand's behalf. The most emotional moment came when Garofalo presented a tribute video featuring Benjamin “Benji” Menendez, who graciously accepted the recognition from his home in Cuba. His message of appreciation to generations of consumers provided a striking contrast to the night's comedy, cash prizes, and games.

Saturday began with VIP admission at 11 a.m., followed by general admission at noon. The nor'easter continued to batter the region with rain and strong winds, but did not keep the approximately 500 people from attending the day's festivities.

Saturday shifted the emphasis toward interaction. Guests could meet manufacturers and industry representatives, explore participating brands' offerings, and visit the Two Guys Cigars pop-up store, with, of course, a cigar branded specifically for the occasion. Perdomo Cigars produced the 2026 New England Cigar Expo limited-edition cigar exclusively for the event at Tabacalera Perdomo in Estelí, Nicaragua, packaged in a deliberately playful 14-count pizza box, with only 300 boxes produced.

The packaging nodded to what would become one of Saturday's most memorable attractions: the Beach Pizza Eating Championship. Eight contestants took the stage for a competition with a $5,000 prize pool. Each contestant received two sheets of pizza, each weighing approximately 3.5 pounds and measuring three feet across, making the challenge as visually ridiculous as it was physically demanding. A 90-pound woman won by consuming 35 slices, nearly seven pounds of pizza, to claim the prize.

Tony V, a Boston-area comedian, served as master of ceremonies, providing play-by-play commentary as contestants battled through slice after slice. For traditionalists used to cigar events that consist primarily of seminars, tastings, and manufacturer tables, it was probably hard to imagine a less conventional premium tobacco gathering, but that was precisely the point.

Then came Eric “Badlands” Booker. The professional competitive eater, Guinness World Record holder, and popular YouTube personality brought another unusual dimension to the afternoon. Known for his speed-drinking exploits, Booker attempted two records during the Expo. Using a straw, Booker consumed one liter of tomato sauce in approximately 42 seconds. Garofalo believed the performance unofficially surpassed the existing benchmark, though Guinness World Records has not yet officially certified it. Booker also attempted to consume New England clam chowder at a record-breaking pace, leaving the audience somewhere between fascination and nausea.

Perhaps the most impressive achievement of the 2026 New England Cigar Expo was not the $25,000 game show prize, the Hall of Fame induction, the pizza championship, or the world-record attempts. It was the fact that all of those things could coexist around a cigar.

The weekend showed that a premium cigar event does not have to choose between artisanship and entertainment. It can celebrate both. Garofalo and his Two Guys Cigars staff created an event that can function at that scale while maintaining the relaxed social atmosphere that makes cigar culture unique. The numbers tell part of the story: roughly 400 guests Friday night, 500 on Saturday, 16 cigar manufacturers and visitors arriving from around the world, but numbers cannot fully explain why people were willing to brave a nor'easter to attend. The answer is in the experience.

A cigar is rarely just a cigar. It is an excuse to sit with someone, tell a story, laugh, reconnect with old friends, enjoy a good cigar, and sometimes, apparently, watch someone eat seven pounds of pizza or drink a liter of tomato sauce.

In an industry built on tradition, Garofalo has deliberately created something unconventional: a cigar event that does not just sell the idea of premium tobacco, but celebrates the entire culture around it.