2 days in Pleasantville Itinerary

2 days in Pleasantville Itinerary

Created using Inspirock Pleasantville trip itinerary planner

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— 1 night


Pleasantville ©
Pleasantville is a village in the town of Mount Pleasant, in Westchester County, New York. Start off your visit on the 21st (Thu): steep yourself in history at United States Military Academy, look for gifts at Rockland Bakery, and then immerse yourself in nature at Rockefeller State Park Preserve. On your second day here, explore the world behind art at Storm King Art Center, do a tasting at Brotherhood - America's Oldest Winery, and then learn about winemaking at Warwick Valley Winery.

To find maps, where to stay, other places to visit, and other tourist information, you can read our Pleasantville trip planner.

In June in Pleasantville, expect temperatures between 78°F during the day and 60°F at night. Wrap up your sightseeing on the 22nd (Fri) early enough to travel back home.

Things to do in Pleasantville

Parks Wineries Nature

Side Trips

Rockland Bakery, Storm King Art Center, Brotherhood - America's Oldest Winery, United States Military Academy Visitor Center, Warwick Valley Winery
Find places to stay Jun 21 — 22:
Highlights from your plan
Rockefeller State Park Preserve ©
Rockefeller State Park Preserve
Brotherhood - America's Oldest Winery ©
Warwick Valley Winery ©
Warwick Valley Winery