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The 2026 World Series is officially underway, with the Milwaukee Brewers and Tampa Bay Rays facing off for baseball's biggest prize. And with neither team having ever won a World Series title, history is guaranteed to be made! But even if you're not a diehard baseball fan, there's plenty to love about America's pastime.
Baseball has inspired some of the most beloved stories ever told, from heartwarming underdog tales to remarkable true stories of athletes who changed the game forever. So, in celebration of the MLB World Series, we're stepping up to the plate with six home-run picks across movies, books, and TV that capture the magic of baseball.
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A League of Their Own: Must-Watch Baseball Shows
Some of baseball's most fascinating stories deserve more than two hours to tell. These two shows bring the sport's rich history and unforgettable characters to life.
The Captain
Streaming on ESPN
How did Derek Jeter become one of the most beloved athletes in New York City history? This revealing seven-part ESPN documentary traces the Yankees legend's rise from promising rookie to five-time World Series champion, featuring candid interviews and behind-the-scenes stories that offer an eye-opening glimpse into his extraordinary career.
A League of Their Own
Streaming on Prime Video
During World War II, women stepped up to the plate to keep professional baseball alive. Inspired by the real-life All-American Girls Professional Baseball League and the beloved 1992 film, this acclaimed series stars Abbi Jacobson and D'Arcy Carden in a funny, heartfelt celebration of friendship and perseverance.
Hotel Spotlight
Together with Inside Hotels
Loews Chicago Hotel
The Vibe: Lakeside city living
The Location: Chicago, IL
Instaworthy Accommodations:
Chicago sightseeing starts at the window at Loews Chicago Hotel, where 400 refreshed rooms and suites frame the skyline, river, or Lake Michigan. This Streeterville stay puts Magnificent Mile shopping five minutes away on foot and Navy Pier just ten. Fuel up with breakfast at ETA Restaurant or espresso from For Five Coffee Roasters before heading out. Back at the hotel, swim a few laps in the 75-foot indoor lap pool or settle beside the lobby’s dramatic fireplace. For extra room to spread out, book one of the 25 suites, each with a separate living area.
Take Me Out to the Bookstore
Whether you're a lifelong baseball fan or simply love a good story, these two books have plenty to offer readers of all stripes.
The Cactus League
by Emily Nemens
On the surface, Jason Goodyear has it all: fame, fortune, and a thriving baseball career. But beneath the Arizona sun, his life is falling apart. Emily Nemens' acclaimed debut novel is a compelling, character-driven drama about the complicated lives behind America's pastime.
The Boys of Summer
by Roger Kahn
Step back into baseball's golden age with sportswriter Roger Kahn, who covered the legendary Brooklyn Dodgers during the 1950s. Blending firsthand memories with intimate portraits of players like Jackie Robinson, this beloved nonfiction classic is widely regarded as one of the finest baseball books ever written.
Hotel Spotlight
Together with Inside Hotels
The Brass Key Guesthouse
The Vibe: Cape Cod conviviality
The Location: Provincetown, MA
Instaworthy Accommodations:
A collection of historic homes sets the scene at The Brass Key Guesthouse, a 21-and-over retreat one block from Provincetown’s shops and restaurants. Start with complimentary hot breakfast in the gardens or beside the heated pool, then borrow a bike, kayak, or paddleboard, all included with your stay. Rooms come with espresso makers and mini refrigerators for leisurely mornings between adventures. Return for a soak in the hot tub or the daily hosted social hour before heading to Shipwreck Lounge. With signature cocktails, an outdoor firepit, and an indoor fireplace, it makes settling in feel like going out.
Baseball's Greatest Big-Screen Hits
From Oscar-nominated blockbusters to critically acclaimed indie gems, baseball has inspired some truly incredible movies. These two prove that great sports stories don't always need a dramatic ninth-inning home run.
Moneyball
Streaming on Hulu and Disney+
When Oakland A's general manager Billy Beane faces the challenge of building a winning team on a shoestring budget, he turns to an unconventional strategy: data analytics. Brad Pitt and Jonah Hill star in this Oscar-nominated sports drama about the revolutionary approach that changed baseball forever.
Eephus
Streaming on Prime Video
When their beloved baseball field faces demolition, two rec-league teams gather for one final game. Writer-director Carson Lund's bittersweet debut transforms a simple afternoon on the diamond into a funny, nostalgic meditation on friendship and the passage of time. It’s a true hidden gem with a perfect 100% Rotten Tomatoes score.
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