Why It’s Great
You can immerse yourself in culture—starting with gallery hopping throughout downtown. Begin at The Beck, a design gallery on Mill Street (founded by husband-and-wife team Ana Claudia Schultz and Aaron Smyle) that showcases Hudson Valley makers and artists. Many pieces on display are also for sale. In the Rhinebeck Courtyard (the entrance is between Allure Aveda Concept Salon and Indian restaurant Cinnamon) is Betsy Jacaruso Studio, an airy gallery featuring Jacaruso’s landscape paintings. Art Gallery 71 on East Market Street showcases pieces from local painters and photographers, plus monthly featured artists. If you’re a creative, stop by the Rhinebeck Artist Shop (for art supplies) and Oblong Books (for inspiring coffee table books and literature). On weekends, The CENTER for Performing Arts hosts musicals, plays, and dance recitals. Past productions of “The Lightning Thief: The Percy Jackson Musical” and Rhinebeck Theatre Society’s “Little Women” were a hit. This spring, The CENTER is showing “Hamlet,” a classic Shakespearean tragedy, from March 8–17. (There is also a Saturday Morning Family Series for those with kids.)
Ten minutes north of Rhinebeck is the Hessel Museum of Art at Bard College, which curates more than 3,000 pieces by over 570 renowned contemporary artists in its permanent collection. You’ll find feminist works by Janine Antoni, minimalistic paintings by Sol LeWitt, and Christopher Wool’s post-conceptual pieces. When the semester is in session, the Center for Curatorial Studies gallery often features student work genres of sculpture, print photography, and painting. In April, the Hessel Museum will open a variety of exhibitions curated by graduate students.
Make the tough choice between Cinnamon and Aroi Thai—both have aromatic dishes with plenty of coconut milk, spices, and flavor. We also recommend Le Petit Bistro for its great brunch, where fried oysters, buttermilk pancakes, and potato-crusted quiche are on the menu.
While Pretty To Think So’s seafood is a treat, we suggest checking out the bar. The cocktails are seasonal and distinct—the Never Fully Dressed with vodka, pink vermouth, absinthe verte, and Creole bitters is unique—and there are low-ABV and zero-proof options, too.
Why It’s Great
Though not the original location of the 1969 Woodstock Music and Art Fair (some out-of-towners get it confused), this vibrant Ulster town has a fantastic music scene with roots in folk and rock: Bearsville Theater was originally a community for legends like Bob Dylan, Janis Joplin, and The Band. Today it has nighttime performances in a renovated theater—but during the day you can tour the grounds to learn about legendary manager Albert Grossman and Bearsville Studios, or relax in Bearsville Park (which has picnic tables for snacking and outdoor live music). Beginning in April, you can book a walking tour co-hosted by Rock Junket Tours. For over two hours, you’ll hear fascinating stories, see rare photography and album art, and view landmarks like Dylan’s “White Room” on Tinker Street. (The space was recently converted into an acoustic instrument shop called Folkadelic.) Bearsville also hosts Sunday jazz brunches from 11 a.m.–3 p.m.
In April, Colony—an intimate circa-1929 space on Rock City Road—opens its outdoor beer garden for live music (from bluegrass groups to solo indie artists) and pub food. And Woodstock Playhouse on Mill Hill Road features shows—like the Woodstock Symphony Orchestra and tribute concerts by Rock Academy—along with film festivals and plays in the warmer months.
On March 1, the Woodstock Artists Association & Museum unveils its members’ spring exhibition and Suzy Sureck’s “Tread Lightly,” an installation that highlights the root systems of trees by using sound and visual graphics. For some retail therapy, we like Shop Little House for barware and blankets, Golden Notebook’s great selection of reads, and the sustainable skin and bath products at Lovewild Design. Make sure to stop by Woodstock Waterfall Park for a pretty view of the Tannery Brook.
If you arrive around brunch time, hit up the Mud Club or Moonrise Bagels—the bagel sandwiches are some of the best around. Grab a heartier bite at Millstream Tavern (for weekend jazz brunch), Yum Yum Noodle Bar, Sharkie’s (best known for their meatball heroes), or Tinker Taco (chorizo y papas is one of our favorites).
Enjoy happy hour at Early Terrible. This whimsical bar—with carved trees and twinkling chandeliers just about everywhere—is straight out of a fairy tale.
Why It’s Great
This Orange County gem has a great mix of options for those looking to brewery hop or eat a variety of cuisines. Warwick also has plenty of food-centric shopping including Warwick Chocolate Company, a sweets shop with craft bonbons and heart- or animal-shaped treats; Warwick Valley Olive Oil Co. for unique oils and vinegars, plus sea salts, spices, and local maple syrup; Candy Apple Shoppe which sells caramel apples and chocolate-covered pretzels; and Fizzy Lifting Soda Pop Candy Shop. Don’t miss the homemade kimchi and sauerkraut at Drifter Ferments, which also has an on-site café and starting in mid-May, head to the beloved Warwick Valley Farmers Market.
There’s something for every type of foodie here. ROAM Food Truck serves up delicious salads and sandwiches (try their Cubano) and frequents spots like Warwick Valley Winery & Distillery and Drowned Lands Brewery. Known for its 40-plus beers on tap, Eddie’s Roadhouse has a menu full of seasonal comfort food from a French toast fried chicken sandwich to pistachio-crusted salmon with saffron mushroom risotto. Traveling with a furry friend? Head to Fetch Bar & Grill, a lunch spot decked out in all things canine with famous Philly cheesesteak egg rolls and punny cocktails. There’s also Wolfies of Warwick for pressed pastrami or brisket sandwiches. In the mood for Asian? Go for the pad thai at Warwick Thai. For dessert, try Dream Donuts (known for mini donuts) and Noble Pies (the “Leslie’s Lime” key lime pies are fantastic).
It’s always hoppy hour in Warwick and the neighboring town of Chester. Rushing Duck Brewery (Chester) has just about everything—from Electric Gremlins (golden ale) to an Oatmeal Stout—so getting a flight (or two) is recommended. People come for the fruity IPAs and stay for the artisanal pizza and live music at father-daughter owned Tin Barn Brewing (Chester). Ten minutes south in Warwick is DUBCO Acres (a sister location to Long Island’s popular Destination Unknown Beer Company) with a taproom in a converted dairy barn and outdoor patio space with views of rolling hills. Sip on Four Corners (farmhouse ale) or Dub Light (lager)—and pair it with nachos or hummus platters. You’ll find a hip, minimalist tap room overlooking Wickham Lake at Drowned Lands (Warwick). All their beer—from fruity Demure (farm hand saison) to Pavonia (hazy pale ale)—is aged in oak barrels to encourage unique fermentation.
Why It’s Great
It’s an ideal area for adventuring with the family. The 26-mile Harlem Valley Rail Trail (you can hike or bike) cuts right through Millerton. The entrance is on South Center Street and there’s plenty of parking. If you have the stamina (and the kids aren’t bored yet), trek 3 miles north on the HVRT to Taconic State Park, where you’ll find more trails and picturesque Rudd Pond. (You can also drive there.) Iron Mine Pond Loop is a pretty hike with water features and views of the surrounding mountains. At Rudd Pond, the kids can go fishing and boating; it has beachfront swimming starting Memorial Day Weekend. You can also take a 20-minute detour to Trevor Zoo—a student-assisted zoo with endangered and exotic animals—in Millbrook.
Downtown is home to Oblong Books and Oblong Jr. Toys and Books, a cute shop with plenty of picture books and middle grade reads, puzzles, and more. Adults will enjoy wandering around the Millerton Antique Center, which showcases vintage finds—furniture, vinyl, rugs, and more—from over 35 dealers. Westerlind, a fashion boutique, has chic outdoor apparel and gear. If you have the time or the weather turns, catch a flick at The Moviehouse. There are several showtimes each day including both kid-friendly and award-winning films.
Grab lunch at Oakhurst Diner or Four Brothers Pizza Inn. The diner is known for its farm-to-table fare (the chicken lemongrass dumplings are a favorite) in a retro steel space, plus it has outdoor seating come spring. The Pizza Inn is a Valley institution—share a pie or go for pastas, sandwiches, and chicken fingers.