You can bet the Oscars online from Massachusetts and all the New England states using any number of internationally-based websites. Massachusetts itself does not host online sports betting sites that would offer Oscar betting.
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In May 2018 the U.S. Supreme Court ruled that states could begin offering sports betting, including via the Web. While the Oscars may not seem like a sports betting event (and indeed it is not), for years the awards show has been a pivotal part of sportsbook offerings throughout the world. In fact, outside of the U.S. Presidential elections and a handful of other big political events like Brexit, the Oscars has long been the most bet on single day non-sporting event.
Rhode Island is the only New England state thus far that is home to sportsbooks (2) but neither is online and they do not offer betting on the Oscars.
Massachusetts and Connecticut are each considering allowing sportsbooks to operate within their borders, however, it is not known yet if they would go online or if they would allow betting on the Oscars. This could occur prior to the 2020 Academy Awards. In the meantime, you can simply place your Oscar bets here.
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- Jordan Bach, Gambling911.com