9 days in Hudson River Valley, West Point & Woodstock Itinerary

9 days in Hudson River Valley, West Point & Woodstock Itinerary

Created using Inspirock United States tour builder
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Make it your trip
Fly to La Guardia Airport, Drive to Tarrytown
1
Tarrytown
— 2 nights
Drive
2
West Point
— 1 night
Drive
3
Hyde Park
— 2 nights
Drive
4
Woodstock
— 3 nights
Fly

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Tarrytown — 2 nights

Tarrytown is a village in the town of Greenburgh in Westchester County, New York, United States. Sleepy Hollow Cemetery and Kykuit will appeal to history buffs. Your cultural itinerary includes sights like Lyndhurst and Old Dutch Church and Burying Ground. The adventure continues: contemplate the long history of Van Cortlandt Manor.

For photos, traveler tips, where to stay, and tourist information, read Tarrytown trip planning website.

Atlanta to Tarrytown is an approximately 5-hour combination of flight and car. You can also drive. Traveling from Atlanta in October, expect Tarrytown to be a bit cooler, temps between 65°F and 49°F. Wrap up your sightseeing on the 17th (Mon) to allow time to travel to West Point.
more
Historic Sites · Museums · Parks
Side Trips

West Point — 1 night

West Point is the oldest continuously occupied military post in the United States. Kick off your visit on the 18th (Tue): browse the exhibits of West Point Museum and then explore the historical opulence of Bannerman Castle.

To find photos, where to stay, traveler tips, and other tourist information, refer to the West Point travel app.

You can drive from Tarrytown to West Point in an hour. Expect a daytime high around 64°F in October, and nighttime lows around 46°F. Wrap up your sightseeing on the 18th (Tue) to allow time to drive to Hyde Park.
more
Historic Sites · Museums
Side Trip

Hyde Park — 2 nights

Hyde Park is a town in Dutchess County, New York, bordering the Hudson River north of Poughkeepsie. Kick off your visit on the 19th (Wed): steep yourself in history at Eleanor Roosevelt National Historic Site, then steep yourself in history at Home of Franklin D. Roosevelt, and then get engrossed in the history at Franklin D. Roosevelt Presidential Library and Museum.

For maps, ratings, traveler tips, and more tourist information, you can read our Hyde Park visit planning tool.

Traveling by car from West Point to Hyde Park takes 1.5 hours. Expect a daytime high around 67°F in October, and nighttime lows around 43°F. Finish your sightseeing early on the 20th (Thu) so you can drive to Woodstock.
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Historic Sites · Museums

Woodstock — 3 nights

Woodstock is the shire town of Windsor County, Vermont, United States. Your inner history buff will appreciate Flume Gorge and Marsh - Billings - Rockefeller National Historical Park. When in Woodstock, make a side trip to see Off-Road Tours in Lincoln, approximately Lincoln away. There's more to do: take an in-depth tour of Billings Farm & Museum and experience rural life at Sugarbush Farm.

For other places to visit, reviews, where to stay, and more tourist information, use the Woodstock sightseeing tool.

You can drive from Hyde Park to Woodstock in 4.5 hours. Other options are to do a combination of bus and train; or do a combination of bus, train, and flight. Traveling from Hyde Park in October, you will find days in Woodstock are little chillier (62°F), and nights are about the same (40°F). Wrap up your sightseeing on the 23rd (Sun) early enough to fly back home.
more
Historic Sites · Nature · Parks · Tours
Side Trip