Your itinerary

5 days in Pittsfield area

Wed, Nov 4 – Sun, Nov 8 · 2 travelers · comfort

New trip

Estimated total

$1,469

Stays$600

Food$600

Tickets$240

Travel$29

≈ $735 per person

1
Wed, Nov 4
Pittsfield area
$315
- 09:461
  The Clark Art Institute
  park
  until 11:01Free 46 min
- 11:082
  Williams College Museum of Art
  museum
  until 13:08~$20/person 7 min
  Lunch at CRUSTPizza restaurant
- 14:233
  Massachusetts Museum of Contemporary Art
  museum
  until 16:23Free 15 min
- 16:314
  Natural Bridge State Park
  park
  until 17:46Free 8 min
Sunset 4:42 PM· golden hour atWahconah Falls State Park
Dinner atStarbucks(Coffee shop café)
Stay near Pittsfield · ~$150Booking.com Airbnb
2
Thu, Nov 5
Pittsfield area
$353
- 09:151
  Pleasant Valley Wildlife Sanctuary
  park
  until 10:30Free 15 min
- 10:422
  Tanglewood
  park
  until 11:57Free 12 min
  Lunch at Shaker Mill TavernAmerican restaurant
- 13:063
  The Mount
  museum
  until 15:06~$20/personOpen 10:00–17:00 9 min
- 15:204
  Norman Rockwell Museum
  museum
  until 17:20~$20/person 14 min
Sunset 4:41 PM· golden hour atSheffield Covered Bridge
Dinner atXicohtencatl Restaurant(Mexican restaurant)
Stay near Pittsfield · ~$150Booking.com Airbnb
3
Fri, Nov 6
Pittsfield area
$356
- 09:101
  Arrowhead
  museum
  until 11:10~$20/person 10 min
- 11:262
  Hancock Shaker Village
  museum
  until 13:26~$20/person 16 min
  Lunch at Wander BerkshiresCoffee shop café
- 14:533
  October Mountain State Forest
  park
  until 16:08Free 27 min
- 16:454
  Notchview
  park
  until 17:60Free 37 min
Sunset 4:40 PM· golden hour atWahconah Falls State Park
Dinner atStarbucks(Coffee shop café)
Stay near Pittsfield · ~$150Booking.com Airbnb
4
Sat, Nov 7
Pittsfield area
$277
- 09:471
  Searles Castle
  attraction
  until 11:17Free 47 min
- 11:412
  Taconic State Park – Copake Falls Area
  park
  until 12:56FreeOpen 00:00–23:59 24 min
  Lunch at Roberto's PizzaPizza restaurant
- 14:063
  Mount Washington State Forest
  park
  until 15:21Free 10 min
- 15:354
  Tri-State Marker
  Tripoint boundary marker for Connecticut, Massachusetts, and New York
  until 17:05Free 13 min
Sunset 4:39 PM· golden hour atBash Bish Falls State Park
Dinner atXicohtencatl Restaurant(Mexican restaurant)
Stay near Pittsfield · ~$150Booking.com Airbnb
5
Sun, Nov 8
Pittsfield area
$168
- 09:571
  Bear Swamp
  park
  until 11:12Free 57 min
- 11:302
  Chapel Brook
  park
  until 12:45Free 18 min
  Lunch at Blue Rock RestaurantAmerican restaurant
- 14:093
  Shelburne Falls Trolley Museum
  museum
  until 16:09~$20/person 24 min
- 16:164
  Bridge of Flowers
  attraction
  until 17:46Free 7 min
Sunset 4:38 PM
Dinner atDelicatesse(Deli café)

Day 1 Day 2 Day 3 Day 4 Day 5

Where the money goes

$1,469

$735 per person · $294 per day

Stays: $600 41%
Food: $600 41%
Tickets: $240 16%
Travel: $29 2%

Cost per day

$356

D1D2D3D4D5

Split costs$735 each

Stays$600paid by
Food$600paid by
Tickets$240paid by
Travel$29paid by

Settle up

Friend 1$106You

Get ready

Book your stays (4 nights)
Reserve a rental car (if you need one)
Share the plan with your group and vote on stops
Buy tickets: Williams College Museum of Art, The Mount, Norman Rockwell Museum +3 more
Check the forecast and adjust rainy days
Download offline maps for your route

How's this plan?

Drag, swap or remove stops; times and costs update instantly. Estimates assume one room per 2 guests, typical nightly rates for your budget level, entry fees only where entry is paid, and gas or transit fares. No flights or car rental. Bookings open on partner sites; we never take payment.