Weekend getaway from New York · #7 of 10
New Haven
Yale's hometown packs free world-class museums, a leafy green and America's most argued-over pizza tradition ('apizza' at Pepe's vs Sally's) into a compact, walkable city two hours up the coast.
Moody Gothic campus architecture, world-class free museums, and America's most fiercely debated pizza, all packed into a walkable coastal city two hours away. Settle the Pepe's-versus-Sally's crown for yourself.
Getting there
Your budget-friendly commuter option. It takes a bit longer than Amtrak but runs constantly, and Union Station is just a quick walk or bus ride from the Green.
Faster and a bit pricier than Metro-North, but totally worth it if you want to sleep in a little later.
Day 1
Yale's historic campus and iconic Wooster Street apizza- 19:00 AMDrive
Train up the coast
Board Metro-North or Amtrak in New York. Settle in as the train hugs the Long Island Sound past Connecticut's shoreline towns, pulling right into Union Station.
📍 Grand Central Terminal, New York
- 210:45 AMSight
Beinecke Rare Book and Manuscript Library
This striking marble box glows a warm amber when sunlight filters through translucent walls. Inside, view a Gutenberg Bible and Yale's rare book collection for free.
📍 Beinecke Rare Book and Manuscript Library, New Haven
Tip · Don't get locked out! Check the hours online before you go, as it closes for university holidays and special events.
- 311:45 AMSight
Yale University Art Gallery
America's oldest university art museum is free to enter. Explore multiple floors to find everything from Van Gogh's Night Cafe to ancient Mediterranean pottery.
📍 Yale University Art Gallery, New Haven
- 41:00 PMFood
Apizza at Frank Pepe's
This century-old Wooster Street icon popularized New Haven's thin, bitter-crust apizza. You must order the white clam pie: fresh clams, garlic, and olive oil on a scorched crust.
📍 Frank Pepe Pizzeria Napoletana, New Haven
Tip · Be ready for a line wrapping around the block on weekends, but don't worry, it moves fast!
- 52:30 PMSight
Wander Wooster Square
Walk off lunch in this leafy, historic Italian-American enclave. Stroll around the lovely central park and pop into the old-school bakeries surrounding Pepe's and Sally's.
📍 Wooster Square, New Haven
- 63:30 PMSight
Yale Peabody Museum of Natural History
Yale's natural history museum is free to enter and boasts one of the country's greatest dinosaur halls. Don't miss the legendary Age of Reptiles mural.
📍 Yale Peabody Museum of Natural History, New Haven
- 75:00 PMSight
Stroll the New Haven Green
Stroll this historic 17th-century town common. It's one of America's best-preserved colonial greens, ringed by three historic churches and Yale's old campus gates.
📍 New Haven Green, New Haven
- 87:00 PMFood
Dinner on Chapel or Crown Street
Hit the lively blocks south of campus on Chapel, Crown, and George Streets. This foodie hub rivals major cities, bursting with everything from cozy wine bars to global small plates.
📍 Chapel Street, New Haven
- 9NightStay
Check in near the Green
Snag a hotel near the Green or Yale campus to stay within walking distance of everything on this trip. No car or rideshare needed!
📍 New Haven Green, New Haven
Day 2
More world-class galleries and round two of the apizza showdown- 109:00 AMFood
Coffee near the Green
Kickstart your day at a cozy cafe near Yale's old campus before easing into a slow, art-filled morning of museum-hopping.
📍 New Haven Green, New Haven
- 1110:00 AMSight
Yale Center for British Art
Explore the largest collection of British art outside the UK. It is housed in a quiet, Louis Kahn-designed building with beautiful skylit galleries, and it's free to enter.
📍 Yale Center for British Art, New Haven
- 1211:30 AMActivity
Browse downtown shops
Wander the vibrant streets around the Green and Chapel Street. It's a perfect mix of independent bookstores, cool vintage shops, and Yale-adjacent boutiques.
📍 Chapel Street, New Haven
- 131:00 PMFood
Round two: Sally's Apizza
Pepe's Wooster Street rival has been slinging coal-fired apizza since 1938. Try the classic tomato pie or another white clam round to compare against yesterday's feast.
📍 Sally's Apizza, New Haven
Tip · A few of these historic Wooster Street joints only take cash, so check their policy before you grab a table.
- 142:30 PMSight
Lighthouse Point Park
Just a short ride from downtown, this shoreline park offers a historic 1840 lighthouse, a classic carousel, and open views over Long Island Sound. It is a nice escape from campus.
📍 Lighthouse Point Park, New Haven
- 154:30 PMFood
Last coffee before the train
Head back downtown for a final coffee or pastry near Union Station before you board your train heading south.
📍 Union Station, New Haven
- 165:30 PMDrive
Train back to New York
Hop on Metro-North or Amtrak at Union Station for a relaxing train ride back down the Connecticut shoreline to New York.
📍 Union Station, New Haven
Where to eat
The legendary, century-old Wooster Street original that's world-famous for its white clam apizza.
Pepe's storied rival since 1938. Settle the score by ordering their iconic classic tomato pie.
These lively blocks just south of Yale punch way above their weight with an incredible, diverse dining scene.
When to go
Yale is in full session and the Green buzzes with life. Be sure to book your weekend dinner spots well in advance!
The campus quietens down with students away, leaving the city all to you, and Lighthouse Point Park's shoreline is absolutely gorgeous.
The ultimate cozy museum weekend. Yale's world-class galleries and libraries are open and warm, whatever the weather.
Good to know
- Be ready for a line at Pepe's or Sally's on weekends. Don't worry: they move fast and are worth every minute!
- Yale's museums and libraries won't cost you a dime, but double-check the schedules as several close on Mondays.
- Almost everything is walkable from Union Station, but you'll want to grab a quick bus or rideshare for Lighthouse Point Park.
- Keep some cash on hand! A few of Wooster Street's historic gems don't take cards, so check before you order.
