Few towns in the Hudson Valley pack as much of a historic punch as West Point does. Back in the days of the Revolutionary War, the fortress was a critical stronghold in Washington’s defense against the British. Perhaps most notably, it served as the western point from which a massive, 75-ton chain stretched to prevent English troops from sailing further along the Hudson.
After the war, West Point opened its doors as the site of the United States Military Academy in 1802. Since then, the location has operated as the oldest continuously occupied regular army post in America.
While the West Point of the present day is a bustling hub for cadets and military leaders, it’s also a must-visit destination for history buffs and Hudson Valley visitors. Read on for a day trip guide to the storied region, then hop in the car for an impromptu blast to the past.
If you plan to visit, make sure to check the academy’s website in advance for potential closures and planned events.
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9 a.m. – Treat yourself to comfort food classics at Andy’s Restaurant
With so much moving and shaking going on at West Point, cadets (and visitors) require grade-A fuel to get it all done. Andy’s, which sits just down the road from the school, delivers with hearty breakfasts and lunches that are just as plentiful on portion as they are on flavor. Early in the day, opt for one of the massive omelets to get you going. The Black Knight Omelet, an ode to West Point’s mascot, is a three-egg, sausage, bacon, ham, onion, pepper, and cheese concoction that should fuel you until lunch. Did we mention it comes with home fries and toast on the side?
281 Main St, Highland Falls
845.446.8736
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10:30 a.m. – Explore local history at the West Point Museum
As you continue to listen to the Hamilton soundtrack, get a historic fix at the West Point Museum. A must-visit for history lovers, the museum is a hotbed for U.S. military artifacts and documents. Take a whirl through the past as you explore detailed exhibits and brush up on your knowledge of the past exploits and endeavors of the nation’s servicemen and women.
2110 New South Post Rd, West Point
845.938.3590
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12 p.m. – Dig into a sumptuous sammie at South Gate Tavern
Just outside the West Point gate (hence the name), this local tavern is a must for authentic Irish pub fare with an incredible array of memorabilia. As for what to order, stick to the classic combination of a hearty sandwich and a perfectly foamy pint of Guinness. It is an Irish pub, after all.
509 Main St, Highland Falls
845.446.8747
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1:30 p.m. – Take a self-guided tour around the West Point campus
West Point is a military academy, but it’s also an open-air museum. Thanks to its 18th-century significance in American history, the site is now a hotbed for local history. After you wrap up with lunch, return to campus to see where the “Great Chain” ran across the Hudson, how Fort Putnam held up since the war, and what the South Battery and Sherburnes Redoubt landmarks look like up close. If you’d rather listen to a pro explain each location’s significance, stop by the West Point Visitors Center to find out when the next tour runs. Reservations for tours are available approximately three months in advance. The History and Tradition Cemetery tour is seasonal, so plan ahead if you want to check that one out.
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4:30 p.m. – Savor sky-high sips at West Point’s Zulu Time Rooftop Bar & Lounge
When crisscrossing campus gets the best of you, kick back before dinner at The Thayer Hotel’s rooftop bar and lounge. Zulu Time, named after a military term that refers to the universal Greenwich Mean Time, is open seasonally from Wednesday through Sunday based on the weather, so check the website or call ahead if you plan to go for a drink. As for what to sip, try something from the ever-rotating lineup of cocktail specials or sip whichever wine the bartender recommends. For serious summer flavor, the Silky Citrus Sour with Tito’s vodka, fresh citrus, tangerine, homemade orgeat, and orange bitters is an absolute delight.
The Thayer Hotel, 674 Thayer Rd, West Point
845.446.4731
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7 p.m. – Wine and dine at MacArthur’s Riverview Restaurant
By the time dinner rolls around, skip the hassle of packing everyone into the car and stay onsite for a feast at MacArthur’s. The white tablecloth eatery is a dream for anniversaries and special occasions, so keep the ambiance in mind when planning your outfit (i.e. no jeans). Once you’re seated, begin the meal with appetizers like deviled eggs and beet carpaccio, then get ready to dig into butternut squash ravioli or boneless beef short rib with cheese grits for the main meal.
The Thayer Hotel, 674 Thayer Rd, West Point
845.446.4731
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9 p.m. – Sleep better than a president at The Thayer Hotel
Thanks to an endless stream of familial visitors and upstate weekenders, the Thayer Hotel has luxury overnights down pat. With 151 guestrooms and suites, the hotel can accommodate a variety of party sizes and price points. Rooms vary to house a variety of parties, with everything from deluxe and premium guest to executive junior, super, presidential, and bridal suites. If you visit on Sunday morning, do yourself a favor and hit MacArthur’s Champagne brunch before you leave. The spread is divine, as are the bottomless champagne, mimosa, and Bloody Mary offerings.
674 Thayer Rd, West Point
845.446.4731
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