Yale Daily News

About 40 Yale undergraduates will embark Wednesday on a four-day, 77-mile walk to New York City for October recess.

Organizers plan to start the journey at the Women’s Table on Cross Campus and finish at Grand Central Station in Manhattan. Last week, the organizers sent an itinerary to the entire student body for those interested in joining. The schedule includes rest stops at Dunkin’, nighttime activities at a Sky Zone trampoline park and lodging at three hotels along the route.  

“We have every ounce of confidence that each of our peers who wish to complete the walk will not only succeed but will also find cherished memories along the way,” Joshua Li ’26, one of the organizers, said.

A color-coded map and seven-page guide for the trip explained behavioral expectations, daily itineraries, a suggested packing list, estimated hotel costs and a disclaimer about safety. The guide suggests a budget of around $205 to $330 per person to cover lodging, lunch and dinner. 

The route as mapped out by the organizers follows the Metro-North Railroad through coastal cities, which allows students to opt out of the journey midway if necessary. The organizers closed sign-ups on Oct. 12 after roughly 40 students submitted interest, Li said. 

Li coordinated the trip alongside Michael Zhao ’26, Brian Moore ’26 and Freeman Irabaruta ’26. The idea for the trip originated last semester in a rowdy late-night conversation between Moore and Irabaruta.

“One of us was almost certainly sleep-deprived, and the other not entirely sober. It’s in these moments that our best and worst ideas originate,” Moore said. 

Moore and Irabaruta have a history of performing challenges, Moore said. One semester, they both swore off elevators. Another time, they dared each other to start up conversations on every public transit ride. 

But the walk to New York is their boldest venture yet, Moore said. 

According to Moore, the preparation for the walk was a time-consuming process itself that required more than 10 hours to create the route and organize the schedule. 

“I pushed aside schoolwork and buried myself in Bass Library until 2 a.m. for several days,” Moore said. His nights were spent preparing various aspects of the trip, including researching hotels, examining maps through Street View and “tweaking the route for safety.”

Although the trip was intended for the four friends, Moore said he realized that their plan was comprehensive enough to expand to a larger group. 

“I thought the trip could be even more meaningful if it were open to anyone who wanted to be a part of it,” he said. 

Rory Bricca ’26 found out about the trip from the campus-wide email. He thought it was a prank until he reached out to Li and read the guide. Bricca decided to join, even though it meant rescheduling a meeting and adjusting his fall break plans. 

Bricca has some past experience from walking a 10-day portion of El Camino de Santiago — a historic Spanish pilgrimage trail — and leading First-Year Outdoor Orientation Trips, or FOOT, at Yale. 

“I have found my FOOT trips to be a really great way to bond with a group of people you might not ordinarily interact with on campus, so I think that’s what I’m looking forward to most,” Bricca said. At the same time, he said he is worried about pain in his feet, and hopes the route will be scenic.

Li acknowledged that the journey will not be easy. However, drawing on his experience biking 140 miles from New Haven to Boston during a previous fall break, he agreed with Bricca’s perspective about how the group walk will build community.

“There are no better people than both friends and strangers to share an unexpected adventure with,” Li said. “We hope that this journey will serve as a testament to what Yalies can do when we do it together.”

A train ride on the Metro-North from New Haven’s Union Station to Grand Central takes around two hours.