Posted on December 31, 2017 and last updated on January 08, 2018

Smiling Hill Farm, Westbrook


  • Preserve Size: 500 acres
  • Trail Mileage: 15 miles
  • Pets: yes
  • Difficulty: easy
  • Sights: fields, farm, woods

This is a great farm, especially for kids to visit in the summer. It’s nice to have a big system (roughly 15 miles of groomed tracks) close to the city, but the day I went, the trails were in rough shape — despite the snow being light and fluffy. They were all chopped up and not groomed well. But my GPS stopped working in the cold, which is also perhaps why the groomers weren’t out. I don’t have a self-made map, but the farm has plenty to give out to skiers. Perhaps it’s wise to call ahead to get a sense of the trail conditions?

Directions: The address is 781 County Rd, Westbrook. Drive up the hill and park in the small lot to the right (there will be a sign for x-c trails to direct you). The ski center is on one side of the lot, closer to the woods. You can also pick up lunch after your ski at the farm’s little shop and lunch place.


Let me know if you have any trail updates or corrections!