Weekend Getaways
Westchester Weekend Getaways — Day Trips & Overnights
Westchester's weekend geography punches above its size: Hudson-facing river towns (Tarrytown, Sleepy Hollow, Irvington), the Bedford/Pound Ridge horse country, and day-trip access to the Hudson Valley, Connecticut shoreline, and Hamptons. This pillar covers the weekend-template side: which Westchester weekends work without leaving the county, and which routes make sense for day trips or overnights further afield.
Westchester Weekend Getaways, Local & Beyond
Westchester has strong local weekend options and easy day-trip access to surrounding regions. A cannabis-forward planning guide.
3 min read
Westchester Historic Village Cannabis Weekend, Tarrytown to Piermont via Sleepy Hollow
Tarrytown, Sleepy Hollow, and the short hop across to Piermont run a historic-village template that pairs with a slower evening rhythm. Here is the weekend shape.
5 min read
Westchester Cold-Weather Cannabis Getaway, Late-Fall Through Winter
Late November through early March, Westchester north-county rentals run a fireplace-heavy template that rewards a slower pace. A cold-weather cannabis getaway plan from a local perspective.
5 min read
Peekskill and Croton-on-Hudson Weekend Cannabis
Peekskill and Croton-on-Hudson are the less-touristed northern rivertowns of Westchester. Art studios, Hudson River views, and fewer crowds. Here is the 21+ weekend rhythm.
2 min read
Bedford and Pound Ridge Country-Weekend Cannabis
Bedford and Pound Ridge are the country-estate heart of Northern Westchester. Horse country, stone walls, long driveways. Here is the 21+ cannabis country-weekend rhythm.
2 min read
Sleepy Hollow and Tarrytown Weekend Cannabis Getaway
Sleepy Hollow and Tarrytown make one of the most atmospheric weekend getaways on the Hudson. Here is the 21+ cannabis weekend rhythm.
2 min read
In the queue
- Tarrytown + Sleepy Hollow cannabis weekendComing soon
- Bedford / Pound Ridge horse-country weekendComing soon
- Day trips from Westchester — Hudson Valley routesComing soon
- Connecticut shoreline day trip from WestchesterComing soon
- Westchester + Manhattan evening — reverse-commute editionComing soon
- Westchester hotel weekends worth bookingComing soon