Osceolas

Leaders
Cristian Cavedon (B), Sunhee Bae (B)
Program
Winter School
Type
Hiking
Terrain level
B
Trip date
Saturday, January 17th
Difficulty rating
Hard
Prerequisites
One winter hike with experience with layering in sub-freezing temperatures is preferred. Plus experience on longer (8+ miles) 3-season hikes.

From atop of the Osceolas, you will see an immersive view of the White Mountains.

Overcome the fate of a boring weekend in Greater Boston, and find new life atop two New Hampshire 4,000 footers as we hike out-and-back to East Osceola and Mount Osceola.

Details

The winter approach from the north is rated Difficult due to snow and ice, with steep sections north of East Osceola and between the peaks at the Chimney. These conditions make this an excellent opportunity to practice crampon use. We’re looking for participants who have completed similarly difficult 3-season hikes and are eager to try steep, icy terrain in winter.

Route is here. Do not underestimate this hike based on the mileage! It is quite steep and requires decent cardio-vascular fitness. That said, no crampon experience is needed; we’ll teach you!

Requirements

Previous winter hike experience is encouraged, or confidence in your ability to layer in cold weather. You should also feel confident hiking similar mileage and elevation gain with a moderately heavy backpack during any season.

Chances of using all forms of traction (microspikes, snowshoes, and crampons) and intend to practice crampon use on the trail. This is a great opportunity to hone your traction skills!

Notes

Please budget for the following expenses:

  • $5 trip fee

  • up to $15 for gear rentals

  • $20-50 carpooling costs

  • potentially extra if you want to buy food at a rest stop.

If you are an MIT student, financial aid may be available.

Logistics

Mandatory in-person meeting at MIT student center on Jan 15th at 6pm where we will discuss the route, check out the gear you might need and fit your crampons. We will depart Cambridge Saturday morning likely around 5.30am.

We will need drivers for this trip! Please update your car status if you can drive others (to and fro Boston). If not, please select “not driving” or “will drive self.” You must be prepared to rent a car if you have selected “willing to rent.” (MIT provides discounted car rental to affiliates, and we will evenly split rental/gas costs).


Signup

Algorithm
lottery
Maximum participants
7
Signups open at
Jan. 13, 2026, 7 a.m.
Signups close at
Jan. 14, 2026, 9 a.m.
Notes
  1. What is the most recent comparable hike you've completed in the last 6 months? Please include the distance and elevation gain.
  2. Describe your winter hiking experience!
Signups for this trip are not yet open.