Explore Middletown
What to do, where to eat, and the drives worth taking
A short, honest guide to downtown Middletown and the wider Hudson Valley, the places our guests come back for.
No. 01 · Local guide
Eat & drink
Most of these are a walk or a few minutes' drive from Cottage Street.
- 01
North Wind Bread Company
Our favorite daytime stop, sourdough, pastries, breakfast sandwiches, and good coffee.
- 02
Oak & Reed
One of the best sit-down meals in town: seasonal American food, brunch, and cocktails.
- 03
Copperbarn Coffee
Easygoing coffee, brunch, and a relaxed place to sit for a while.
- 04
Clemson Bros. Brewery
A short walk down Cottage Street, burgers, beer, and frequent live music and events.
- 05
Equilibrium Brewery
Craft beer and barbecue with a taproom and beer garden.
- 06
Cosimo's Brick Oven
Reliable brick-oven pizza and Italian, an easy family or group dinner.
No. 02 · Local guide
Family, shopping & entertainment
From a historic theatre downtown to big day-out attractions nearby.
- 01
Paramount Theatre
Historic downtown theatre for movies, concerts, comedy, and live shows, check the calendar.
- 02
LEGOLAND New York
One of the region's biggest family attractions, a short drive toward Goshen.
- 03
The Castle Fun Center
Arcade, bowling, go-karts, and mini golf, a rainy-day or family standby.
- 04
Galleria at Crystal Run
The closest large mall, shopping, a movie theatre, and dining.
- 05
Woodbury Common Premium Outlets
A major outlet-shopping destination, worth the ~30-minute drive.
No. 03 · Local guide
Parks & trails
Easy fresh-air stops, from a quick walk to a proper Hudson Valley hike.
- 01
Heritage Trail
A flat local walking and biking trail, good for a morning out without a big drive.
- 02
Orange County Arboretum
Gardens and seasonal flowers for a slower, peaceful walk.
- 03
Fancher-Davidge Park
A simple Middletown park for fresh air and open green space close to the hotel.
- 04
Storm King State Park
A more serious hike with classic Hudson Valley views, a scenic drive away.
No. 04 · Local guide
Day trips
When you want to make a half-day of it.
- 01
Warwick Valley Winery & Distillery
Wine, cider, food, and live music on a relaxed Hudson Valley afternoon.
- 02
Goshen
A polished nearby village with good dinners and easy LEGOLAND access.
- 03
Newburgh Waterfront
Hudson River views, dinner, and cocktails for a more scenic night out.
- 04
Beacon
Farther afield but a great day trip, galleries, food halls, shops, and river access.