20s-40s Tanglewood Concert Picnic & Berkshires Hiking Weekend

Activity Type: Hiking, Local Walks, & Trail Running | Hiking
Difficulty: 4 - Moderate
Trip Leader(s): Carly Hodes, Jim Lee, Chao Xie, Johan Gace
Registration Type: Application
Please Click Here to RSVP:https://activities.outdoors.org/a5UUN000001PAMz
Audience: 20’s & 30’s; Adults

Description: Weekend Overview: Join us for a weekend of scenic hikes and summer music in the heart of the Berkshires. During the day, we’ll explore Mount Greylock, the highest peak in MA. On Saturday night, we’ll roll out our blankets for a sunset picnic and an open-air concert at Tanglewood , the summer home of the Boston Symphony Orchestra . We’ll be based in 1-2 peaceful group house rentals in Hancock, MA , near Tanglewood and the mountain. Included: Lodging Friday and Saturday nights, ticket Saturday night. Not included: Food, Friday night tickets.

Mount Greylock (Cheshire Harbor Trail) – Saturday, August 16: On Saturday, we’ll hike to the summit of Mount Greylock, the highest peak in Massachusetts at 3,491 feet! Our route will follow the Cheshire Harbor Trail, a serene, wooded trail that climbs gradually to the summit. At the top, we’ll enjoy sweeping views, explore the historic Veterans War Memorial Tower, and have a break for lunch or snacks. 🥾 Trail Info: Trailhead: West Mountain Road, Adams, MA (about 30–35 minutes from our lodging) Distance: ~6.1 miles round trip Elevation Gain: ~1,870 feet Estimated Duration: 3–4 hours (including breaks) Difficulty: Moderate Route Type: Out & back Expect a shaded forest path, some rocky sections, and rewarding summit views. This is a great opportunity to connect with the group while exploring one of the most iconic hikes in the Berkshires. 📍 AllTrails link: Cheshire Harbor Trail to Mount Greylock
Tanglewood Lawn Concert – Saturday, August 16: 🎻 Augustin Hadelich performs Tchaikovsky's Violin Concerto 🎼 Conducted by Anna Rakitina with the Boston Symphony Orchestra 📍 Tanglewood Music Center, Lenox, MA 🕗 Concert begins at 8:00 PM, plan to arrive by 7:00 PM 🎟️ Lawn tickets are included in your trip cost Bring your favorite picnic foods, a blanket or low lawn chair, and enjoy one of New England’s most beloved summer traditions: classical music under the stars surrounded by rolling hills and a lively, festive crowd. More about the concert: BSO Event Page
Sunday, August 17: Optional Local Hike On Sunday we will do an optional local hike, weather permitting.
Lodging: We’ll stay at a comfortable and stylish group house rental in Hancock, MA featuring: Shared bedrooms and bathrooms Fully equipped kitchen for DIY meals Linens and towels are provided.
Meals: No meals are provided on this trip. Please plan to bring your own food for the weekend. The house has a full kitchen available for participants to store, prepare, and cook meals. We encourage participants to coordinate and cook together as desired. Bring food for your Friday dinner, Saturday picnic at Tanglewood, and any breakfasts/lunches you'd like.
What to Bring: Food and snacks for the weekend Blanket or lawn chair (low-profile) for the concert. Lawn chairs are available for rent. Hiking clothes and sturdy shoes Rain gear Layers for cool evenings Personal toiletries and medications Reusable water bottle Flashlight/headlamp Sunscreen and bug spray Cooler or picnic basket (optional) Games, instruments, or fun extras for the house Rain Plan: We will hike in light rain. In event of heavy rain or thunder, we will explore local museums and breweries. For the Tanglewood concert, we will plan to picnic on the lawn, but in the event of rain we will use seats in "the shed", a covered seating area.

Reminder: Please click the RSVP link above to register!