Sports Rivalry Road Trip: New York to Boston
New England is renowned for its fervent sports rivalries—especially those between New York City and Boston. Here’s a road trip guide to experiencing the best of the region’s competitive games
Follow this route along a New York to Boston road trip to experience some of New England’s best sports rivalries among pro, college and local teams.
Fans the world over are familiar with the sports rivalries dividing New England—especially those between New York and Boston. Over more than a century of contention, team allegiances in the two cities have developed some of American sports’ fiercest rivalries—perhaps chief among them, when the Red Sox traded Babe Ruth to the Yankees in 1919. The Red Sox did not win a World Series for 86 years after, beginning the infamous “Curse of the Bambino.” That particular curse was lifted in 2004, but nevertheless, the New England fever for sports rivalries still thrives. And that means you’ll have plenty to do on this New York to Boston road trip featuring some of the top historical and contentious stops.
It’s Giants, Yankees and Three Monkeys in New York, New York
The new Yankee Stadium, built in the Bronx in 2009, replaces the original “House That Ruth Built” and hosts numerous Yankees/Red Sox rivalry games each year.
The prime spot to see the Boston vs. New York rivalry up close is the new Yankee Stadium, which opened in 2009 in the Bronx. It’s not quite the House That Ruth Built, but it replicates many of the details of the original stadium for baseball purists. While there are tons of things to do near Yankee Stadium, you can also check out a newer New England rivalry that formed in 2008 when the Giants beat the undefeated Patriots in Super Bowl XLII—one of the greatest upsets in sports history. See it for yourself the next time the Patriots are across the Hudson at MetLife Stadium. For a more Bostonian crowd, catch a game on one of 11 screens at the Three Monkey’s Bar, “Home of the Boston Fans.” This bar and beer garden in Manhattan features fine craft brewing and is one of the best Red Sox bars in NYC. It’s just one of the many things to do near Madison Square Garden, yet another New York sports centerpiece. If you are looking for additional attractions, our New York travel guide will help you plan your trip.
See the “Battle of Connecticut” in Bridgeport, Connecticut
Catch a race at Daytona International Speedway in Daytona Beach.
Heading north on your New York to Boston sports road trip, there’s an arbitrary line in Connecticut where sports allegiances split. Sandwiched between New York and Massachusetts, the state has no pro sports teams, but New York-Boston sports history and rivalries still intertwine. At Newfield Park in Bridgeport, a small plaque memorializes city native and New York Giants outfielder Jim O’Rourke, who got his professional start with the Boston Red Stockings (now known as the Atlanta Braves) and had the first base hit in National League history. Later, as a minor league team executive, O’Rourke hired one of the first African American players in league history, Harry Herbert, in 1895. But there’s more than baseball in Bridgeport: At the Webster Bank Arena, the name of the game is hockey. The arena is known for its “Battle of Connecticut,” a rivalry between Bridgeport’s Sound Tigers and the Hartford Wolf Pack, respective affiliates of the famed New York hockey rivals the Islanders and Rangers.
Experience a clash as old as Reconstruction in New Haven, Connecticut
One of the oldest rivalries in all of New England is “The Game” between Ivy League collegiate contenders Harvard and Yale.
Looking for a sports rivalry on the collegiate level? Your next New York to Boston road trip stop is “The Game,” as it’s known among the Ivy League student populations supporting Cambridge’s Harvard Crimson and New Haven’s Yale Bulldogs. The teams first played one another to cap the football season in November 1875 and have faced off 135 times since, with the series currently being led by Yale, 67–60–8. The Game wraps up the season for both programs, so if you can nab tickets to The Yale Bowl when the Harvard Crimson roll through, it’s worth checking out one of the oldest sports rivalries in U.S. history. While you’re there, grab a beer-battered cod sandwich at the Sports Haven Bar & Grille and catch a New England rivalry game on one of their four 90" TV screens.
Visit the capital of the sports news world in Bristol, Connecticut
Visit the peaceful town of Bristol to see the headquarters of ESPN, the country’s sports broadcasting powerhouse.
About 45 minutes north of New Haven is Bristol—not especially noteworthy for sports save for one giant beacon drawing the attention of millions on a daily basis: ESPN headquarters. While you’ll need an employee’s permission to get a facility tour, the ESPN North Campus building is an impressive sight, with banners celebrating the best teams in pro sports depending on the time of year. And a popular selfie spot is the red-white-and-black ESPN North Campus sign. About three miles from ESPN headquarters lies Muzzy Field. Opened in 1912 and rebuilt in 1939, it’s one of the oldest ballparks still in operation in the United States. Today, it hosts mostly high school and summer collegiate games, but Boston Red Sox stars such as Jim Rice, Fred Lynn and Butch Hobson honed their skills here in the 1970s and 80s. And just in case you’re wondering—yes, Babe Ruth played exhibition games here with the Red Sox.
Find high-society sports in Newport, Rhode Island
Newport is known for its large mansions and gorgeous views, but you’ll find it also holds a thriving culture of high-society sports.
West of New Haven on your New York to Boston road trip is the peaceful seaside city of Newport, famous for its huge, historical houses and shopping. Sports rivalries in this “Sailing Capital of the World” favor high-society games like golf or tennis, but the city’s enduring sports culture ensures they exist. Not only do marinas fill every March with yachts for the international America’s Cup sailing competition, but Newport is also known as the host to the first U.S. Open golf and tennis tournaments, held here in the late 19th century. One of those host locations, the Newport Casino, now houses the International Tennis Hall of Fame, where you can learn about the origins of tennis and revisit the stories of some of the most controversial rivalries in all of sports. If you want to extend your stay, check out these other affordable ways to navigate Newport.
Before leaving Rhode Island for Boston on your sports road trip, be sure to make a quick stop in Providence—the city where the “Great Bambino” first earned his fame with the minor league Providence Grays in 1914.
Travel the Yawkey Way in Boston, Massachusetts
There’s no shortage of energetic bars inside and outside of Fenway Park, where the Red Sox/Yankees rivalry often takes center stage.
Named after a former Red Sox owner, Yawkey Way (now called Jersey Street) is the former name of a short stretch of road hosting historic Fenway, the oldest park in Major League Baseball. Ask any resident of Boston for the best sports bars around and they’ll point you to “the Green Monstah,” where well-known establishments like Bleacher Bar lie beneath Fenway’s center field, just feet way from Ted Williams’ famous “red seat,” a 500-foot home run marker. Just across Lansdowne Street, one of the top things to do near Fenway Park is grab a drink at Cask ’n Flagon, a raucous venue late at night, but still a great TV-packed sports bar with an extensive beer list as well as excellent views of Fenway from the patio. If the Yankees are in town, you can catch a game at Fenway—root for the home team or tout your Yankee pride at the ultimate away game.
Hotels near Boston, Massachusetts: 17
If you’re planning a New York to Boston road trip (or any sports road trip), you’d be remiss not to check out the rich sports culture of the region. You can also throw on a Yankees or Red Sox hat to support your major league baseball pick, but beware: That rivalry runs deep.