10 Things To Love About Hillsdale, New York

Over the years, we've brought you feature stories on just about all of these 10-plus places we love in Hillsdale, New York, but we're hearing so much about this small, active town these days that we felt it was time to put them all together as a weekend or day trip itinerary. Sitting at the crossroads of the Hudson Valley and the Berkshires (literally the crossroads of Routes 22 and 23), the Hillsdale village center is well worth slowing down for. Pound for pound the main street is one of the most creatively dense business districts around when it comes to vibrant, artistic and thoughtful small businesses. Whether you’re looking for great food, gifts or something for yourself, Hillsdale has it all wrapped up in a nice little package, with a fresh cut flower on top.

1. Hillsdale General Store and HGS Home Chef

Matthew White and Thomas Schumacher created an old-fashioned general store that offers staples as well as higher-end refined home goods and gifts. More recently the couple opened HGS Home Chef across the street in an immaculately restored, now pink, Victorian home. It's filled with the best kitchen equipment and a test kitchen for classes by culinary bigwigs 

2. Passiflora and The Village Scoop  

First, Ken Davis and Kevin Draves opened Passiflora, a welcoming home goods, art and gifts shop with an international approach, offering gorgeous Indian and South Asian items. The goods are a reflection of the personal passions of the shop's owners, who have traveled extensively in the region, taking photos and purchasing items (and also philanthropically helping support micro-economies in remote areas). Davis and Draves then opened The Village Scoop, next door, which serves up more than just delicious scoops. The menu is fun and inventive and includes house-made sodas and even cheese plates. It’s also a cute little rustic hangout that really captures the spirit of Hillsdale.

3. The Copake-Hillsdale Farmers Market

From spring to fall the Farmers Market draws folks from far and wide. It’s a big market under a large pavilion so there’s a lot of room for activities. There’s usually live music and often some manner of entertainment for the kids, and maybe a baby lamb running around. Organizers hold events and fundraisers throughout the year and it’s a natural, unforced gathering place for the community.

4. Roeliff Jansen Community Library

Speaking of community, the Hillsdale Community Library again feels like yet another overachiever given the size of the town. Like the giant armchair sculpture out front, the Library’s commitment to community literacy and diverse programming is oversized. In this modern age, a library can be one of the most important resources in a rural area to bring people together and help them succeed.

5. Tiny Hearts Flower Shop 

The sunny, hardworking couple behind Tiny Hearts might seem like they’ve put together just the sweetest little flower shop you ever did see, but they’re also a creative powerhouse. There are few places putting out more innovative, naturalistic arrangements. Tiny Hearts uses the best of what’s in season on their farm (that’s right, they’re the flower farmers, too) and add surprisingly vivid foraged items and even edible plants from their farm neighbors. The results aren’t loud or overbearing, just stunning.

6. CrossRoads Food Shop

Like so much in Hillsdale, CrossRoads — another early pioneer in Hillsdale's growth spurt — is doing everything right but then also just doing a little extra. For breakfast and lunch, Chef David Wurth cooks up elegant comfort food with some twists and a focus on incorporating lots of the best local produce. Don't miss the killer egg sandwich.

7. Rookie Farm Bakery

Rookie Farm Bakery might be the new kid on the block, but there’s a real old-school country feel to the presentation and the delectable flavors of its wide range of baked goods. Family run, the bakery focuses on comfort classics, using premium ingredients and free-range, antibiotic-free, organic chicken eggs from the family farm.

8. Foxy and Winston 

Here we have one of the more unconventional new businesses in town but owner Jane Buck is certainly in keeping with the Hillsdale trend of respecting the rural past with an updated, stylish approach. Started in Brooklyn, Foxy and Winston is a paper goods store and a letterpress printing and design studio. Buck is using vintage techniques and antique equipment to personalize wedding invitations and other paper goods with a charm and feel only these old techniques can produce.

9. Rodgers Book Barn

Outside of the village center, on Rodman Road, Rogers Book Barn is a secret to some and a legend to others. Owner Maureen Rodgers has been meticulously curating the barn for nearly 50 years. While it’s packed to the gills with used books and records in great condition, there is more method to the madness than one would assume at first glance. Prices are low and the inventory is deep. Most importantly, Rodgers is a lovely resource to talk books with and you’re more than welcome to hang out, read and relax with a cup of free tea. This is a truly special, one-of-a-kind place that deserves a visit.

10. Grillsdale

This culinary event, coming to the Roeliff Jansen Park on August 24, is billed as a redefined hootenany and we can't wait. Back for its fourth year, Grillsdale proudly spotlights the bounty of Columbia and Dutchess counties and the Berkshires — featuring a smorgasbord of grilled small plates from top restaurants, chefs and purveyors from the area. The fest faces the hills, so attendees can watch the sun set while sampling an all-inclusive food and drink menu. If last year is any indication, Grillsdale will sell out fast, so get your tickets now.