Multi-Day Journey Itinerary - Central/Northern Berkshires Woodlands -

4 days hiking/5 overnights

  • Arrive Sunday in the afternoon

    • Meet up with the Berkshire Camino crew and fellow guests at a designated lot where you will park your vehicle for the duration of the event.

    • Attend the Opening Reception (included) featuring local libations with alcoholic and non-alcoholic choices and munchies (including vegetarian). Meet your fellow retreat participants, get to know the Berkshire Camino Crew and cross the threshold into our sacred walking space.

    • Van transport to Lifehouse Berkshires for check-in.

    • Van transport to/from Lenox town center for dinner (included).

    • Overnight Lifehouse Berkshires.

  • Monday - Day #1 Hiking

    • Have breakfast at the Lifehouse Club Room (on your own).

    • Hike approximately 6 miles on the High Road-Yokun Ridge from Lenox to Pittsfield.

    • Picnic lunch (included) during the hike.

    • Transport by van back to The Ruins at Sasafrass Museum in nearby New Lebanon, NY. This is on the MA/NY state border. Dinner is included with lodging.

  • Tuesday - Day #2 Hiking

    • Breakfast at Sasafrass (included).

    • Hike approximately 8 miles at DCR Pittsfield State Forest ending at Berry Pond, the highest natural body of water in Massachusetts.

    • Picnic lunch (included) at Berry Pond at the end of the day of hiking.

    • Van transport to Hotel on North, in downtown Pittsfield for check-in.

    • Relax at the hotel and enjoy dinner on your own. Choose from several nearby restaurants and bars.

    Wednesday - Day #3 Hiking

    • Breakfast in downtown Pittsfield at your choice of locations (on your own).

    • Hike along the Ashuwillticook Rail Trail, unguided for an opportunity to be in your own head and space. Varying lengths for today’s hike are available per person.

    • Picnic lunch (included) in Cheshire.

    • Van transport to The Springs Motel, in New Ashford for check-in.

    • Enjoy the pool and fire pits.

    • Van transport to dinner at a nearby restaurant (included).

  • Thursday - Day #4 Hiking

    • Breakfast at a nearby cafe (on your own).

    • Explore the DCR Mt. Greylock Visitor’s Center.

    • Hike approximately 4 miles on the Cheshire Harbor Trail to the summit of DCR’s Mt. Greylock, the highest peak in Massachusetts. Hike the additional 90 steps to the top of the War Memorial to take in the vista overlooking 90 miles and five states.

    • Lunch at Bascom Lodge (included) at Mt. Greylock summit.

    • Van transport to either The Williams Inn in Williamstown (May and September) or Hotel Downstreet in North Adams (June and October) for check-in.

    • Relax at the hotel prior to our final night dinner reception (included).

  • Friday - Departure Day

    • Breakfast on your own at your place of lodging or nearby cafes. Van transport to your vehicle will be provided after breakfast.

    • Depart for home.