5 days in Hudson River Valley & Stockbridge Itinerary

5 days in Hudson River Valley & Stockbridge Itinerary

Created using Inspirock United States vacation planner

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Route & dates

5 days in Hudson River Valley & Stockbridge Itinerary

Start: Chicago
Fly + Drive:  6​h 15​min
1
New Paltz
— 2 nights
Drive:  1​h 45​min
2
Stockbridge
— 2 nights
bus + Fly:  7​h 45​min
End: Chicago

2
nights
New Paltz

New Paltz ©
New Paltz is a town in Ulster County, New York, United States. Kick off your visit on the 20th (Sun): steep yourself in history at Vanderbilt Mansion National Historic Site, contemplate the long history of Franklin D. Roosevelt Presidential Library and Museum, then steep yourself in history at Home of Franklin D. Roosevelt, and finally take in the views from Walkway Over the Hudson State Historic Park. Here are some ideas for day two: steep yourself in history at Eleanor Roosevelt National Historic Site, get to know the fascinating history of Historic Huguenot Street, then admire the majestic nature at Minnewaska State Park Preserve, and finally step aboard Pride of the Hudson.

To plan New Paltz vacation without wasting time, ask Inspirock to design an itinerary.

Chicago to New Paltz is an approximately 6.5-hour combination of flight and car. You can also drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to New Paltz. Traveling from Chicago in October, you can expect nighttime temperatures to be a bit cooler in New Paltz, with lows of 43°F. Finish up your sightseeing early on the 21st (Mon) so you can go by car to Stockbridge.

Things to do in New Paltz

Historic Sites Parks Nature

Side Trips

Hyde Park, Minnewaska State Park Preserve, Pride of the Hudson, Walkway Over the Hudson State Historic Park
Find places to stay Oct 19 — 21:
Highlights from your plan

2
nights
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Your day-by-day itinerary now includes Norman Rockwell Museum. Start off your visit on the 22nd (Tue): contemplate the long history of Chesterwood Museum, admire the masterpieces at Norman Rockwell Museum, then admire the natural beauty at Naumkeag, and finally look for gifts at Williams & Sons Country Store. Here are some ideas for day two: get a new perspective on nature at New York State Museum and then admire the masterpieces at The Clark Art Institute.

To see ratings, photos, more things to do, and tourist information, you can read our Stockbridge online itinerary planner .

You can drive from New Paltz to Stockbridge in 2 hours. When traveling from New Paltz in October, plan for a bit cooler days in Stockbridge, with highs around 60°F, while nights are about the same with lows around 40°F. Cap off your sightseeing on the 23rd (Wed) early enough to travel back home.

Things to do in Stockbridge

Museums Parks Historic Sites

Side Trips

The Clark Art Institute, New York State Museum
Find places to stay Oct 21 — 23:
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute
Naumkeag ©
Naumkeag

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