The Ultimate Guide to Gambling Like a Pro in Boston

With the Encore Boston Harbor opening this month, gambling fever has struck Massachusetts. Here’s where to get in on all of the action.


Where to get your (legal) gaming on

MGM Springfield: Newish and smallish, this casino in downtown Springfield has table games and a sea of slots right off the highway in western Mass. Now, Springfield ain’t exactly Vegas, but if you’re looking for exciting new restaurants and star-studded entertainment away from the big city, this is the spot.

Encore Boston Harbor: Welcome to the gilded Cadillac of East Coast casinos. Encore won the bitterly contested license to build this new gambling den because it promised to bring the pinnacle of Vegas swagger to the heart of Greater Boston. From the looks of things, it didn’t disappoint.

DraftKings: All the fun of betting on the big game without the hassle of texting your bookie. DraftKings started out as a way to win money playing fantasy sports, but with legal sports betting in the offing, it’s poised to become the site for people who just love beating the spread on game day.

Plainridge Park Casino: Sad to learn that Suffolk Downs is holding its final race this month? It’s not the only place to play the ponies. Plainridge Park Casino, in Plainville, will run harness races three days a week through November. Papa needs a new pair of shoes!

The Lottery: Why schlep out of the city and fight the crowds when you can play your numbers in the convenience of your corner store? Sure, you gotta pay for your drinks, but you’ll probably lose less money in the long run. Nothing wrong with that.


Ask a Pro

Bill Kaplan, founding member of the MIT Blackjack Team, on how to beat the odds.

What should everyone know before stepping foot in a casino?

Blackjack is the only game that you can legitimately beat.

Your MIT team famously made millions through a card-counting system. Can any sucker learn how to do that?

Honestly, just about anyone with a high school education can learn—it’s just some memorization. Even so, beating the house is hard to do as an individual. Your advantage is about one percent.

Do you really get roughed up in the back room of a casino if you win too much?

Every casino will eventually kick you out. By the time we were playing, though, most places were owned by public companies, so they’d just tell us to go play somewhere else.

The Do’s and Don’t’s


Play Powerball: The 1-in-292-million odds mean you have a better chance of finding buried treasure.

Take a date to watch you lose at poker.

Wager against Governor Charlie Baker, who is hot to see legal sports betting land in Massachusetts.


Give the state’s two new casinos a shot: Even if you lose, there’s always the buffet.

Take a date to dinner and a casino show.

Take the 8-1 odds that the Pats will win the Super Bowl in 2020: Every year could be Brady and Belichick’s last together—’nuff said.