Kennedy Park and Hotel Aspinwall Lenox

By Western Mass Hilltown Hikers (other events)

Saturday, February 25 2023 10:00 AM 2:00 PM EDT

#hikethehilltowns with us!

Kennedy Park and Hotel Aspinwall in Lenox 10:00 am to 2:00 pm
GPS Location: 42.370620, -73.280243 Trailhead and Parking 

Hike Rating: Moderate, approximately 3.5 mile loop with rolling terrain, options for more after the main hike.

Join us for a historic narrative by Tom Hoffman. Learn about the history of Hotel Aspinwall as we hike on several trails including the hotel stables, garage, hotel site, staff housing, laundry, Woolsey homestead, balance rock, and stonehenge. 

The hotel was built in 1902 at a cost of $410,000 and was the former 44 acre estate of Edward Woolsey who owned 500 acres and created eight miles of trails known as Woolsey Woods. The grounds included a view of the valley toward Tanglewood, many bridle paths and carriage roads, 400 guest rooms, golf course, baseball field, movie theatre, newsstand, laundry and a restaurant. It burned to the ground in 1931.

Please Register per car load on Hike is free and volunteer lead, suggested donation is $5.00.  Maps and bottled water provided. Well behaved dogs are allowed. Please bring crampons, hiking poles and a snack. We hike rain or shine. Be prepared for winter conditions and water, roots, rocks and mud on the trail. More details are on

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See all our events, maps, blog and photos at For more hike information email: [email protected] or call/text 413-302-0312.   Follow us on Facebook, Instagram, Meetup, YouTube, TikTok Pinterest and Twitter.  Search our hashtags #westernmasshilltownhikers #hilltownhikers and #hikethehilltowns Please keep our beautiful places clean and carry in and carry out. We are a non-profit 501C(3) organization incorporated in the State of Massachusetts. Tax ID #86-2532249.

Tees, hoodies, hats, window stickers, patches and photos will be for sale at the hike, the complete free catalog of printed hiking maps will be there too.  See all our events, maps, blog and photos at 

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Mission Statement: Western Mass Hilltown Hikers, Inc. is organized exclusively for charitable and educational purposes to engage in all legal activities relating to the development, maintenance and operation of recreational hiking and outdoor adventure in Western Massachusetts.  We are a non-profit 501C(3) organization incorporated in the State of Massachusetts. Tax ID #86-2532249




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PO Box 3 Chester, MA 01011