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What to Do in Chatham: How to Spend 24 Hours in the Upstate Village

Above image by Katie Chirichillo

Day trips to the Columbia County town are all about small businesses, convivial restaurants, and celebrations that unite the community.

Driving into Chatham is an unusual sensation – at least the first time. As if you ventured just a little too long on Route 66 (or the Taconic, if you’re so inclined), the moment you finally pull into town seems like a grand arrival and more like a homecoming. It’s an odd feeling for anyone who’s never visited before, although it’s not an uncomfortable one. Similar to the atmospheres in places like Cold Spring or Red Hook, Chatham embraces that covetable mix of sleepiness and vibrancy that lures people to the Hudson Valley as a whole.

An easy jaunt from Art Omi and Hudson, Chatham is a destination in its own right. Its population may be bitty, but its Hudson Valley history and contemporary culture are grand. In one calendar year alone, the town welcomes visitors from far and wide for no less than five community celebrations that spotlight seasonality and local makers.

Craving a day trip to the village once known as Groat’s Corners? Be sure to tag us @HudsonValleyMag on Instagram as you discover Chatham’s hidden corners.


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Have some of our @pieconicny pie for breky!!

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9:30 a.m. – Savor all the good things at Main St. Goodness

It doesn’t get much better than Irving Farm coffee and Pieconic pie for breakfast. Luckily, you can find them both at Main St. Goodness, Chatham’s community café that started as a dedicated pie company and transformed into a one-stop shop for sweet treats in a small-town environment.

Begin the day with a slice of pie, which you’ll have to narrow down from flavors like fruit shortbread crumble, backyard apple, and gluten-free chocolate cream, to name only a few. Savory quiches and tarts are on the menu as well, and “guppies,” or small-scale pies, are just the thing for anyone who prefers mini treats to their full-size originals.
20 Main St, Chatham
Mon-Thurs 8 a.m. – 6 p.m., Fri-Sat 8 a.m. – 7 p.m., Sun 8 a.m. – 5 p.m.

10:30 a.m. – Discover the history of Chatham

The village that was once known as Groat’s Corners, after early settler Captain Thomas Groat, in the early 1800s has not forgotten its historic roots in the Hudson Valley’s train-centric history. Although the village’s Union Station closed down operations in 1972 after serving as a critical hub for train lines between Boston and Albany, the building lives on as a Community Bank, N.A. at 5 Depot Square.

Nearby, the 1811 Inn at Central Square is Chatham’s oldest building. Swing by to ogle the original architecture and read the New York State marker, which explains that the building was once known as Groat’s Tavern. From there, meander to the slightly newer Chatham Public Library. Built in 1905, the library boasts an original Tiffany window that’s magnificent to behold on a sunny day. Whatever you do, make a point to walk by the striking clocktower at the top of Main Street. It dates back to 1872 and is the stuff of Instagram dreams.

12:30 p.m. – Get your gluten (or gluten-free) fix at Our Daily Bread Deli

If you’ve ever sampled Our Daily Bread’s yeasty confections, you probably know that the deli is the place to go for bready goodness in Chatham. If not, trust us on this one. ODB does bread and baked goods so well that you may even consider returning to the deli for breakfast the following morning. In the meantime, dig into Mediterranean-inspired mains like falafel with hummus and lemony coleslaw or the ODB Reuben with house-smoked pastrami and corned beef. If breakfast is what you crave, the deli’s early bird menu is available all day and features top-notch shakshuka, challah French toast, and avocado toast with – wait for it – fried jalapeño.

For gluten-free eaters, the deli’s aptly-named sister brand The Gluten Free Bakery hits a home run with plush loaves that contain absolutely zero wheat. GFB’s baked goods are available at Our Daily Bread, which means the deli is ideal for diners with any sort of dietary restriction.
116 Hudson Ave, Chatham
Wed-Sun 8 a.m. – 5 p.m.


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2 p.m. – Shop your way through town

Along Chatham’s quaint sidewalks, independent shops plays host to local passersby and far-away visitors alike. As you walk off lunch throughout the afternoon, make a point to pop into the Chatham Bookstore, which has kept bookworms happy for more than 40 years with an ample selection of new titles and visiting authors. For crocheters and knitters, The Warm Ewe is a slice of paradise that stocks yarns and fabrics galore, along with the tools to turn them into treasures.

Right down the street, Bimi’s Cheese Shop is a can’t miss destination for anyone who can’t get enough cheddar and charcuterie. The store’s artisanal selection is ever-changing and full of specialty selections, so make an effort to venture out of your comfort zone and try something new. Better yet, ask the staff what their favorites are.

4 p.m. – Celebrate the arts your way

For a relatively small town, Chatham boasts an incredible array of art-oriented attractions. On the shoppable end of the spectrum, aMuse Gallery devotes its focus to eccentricities that catch the eye and invite questions and reflections. Film and history buffs will want to make a beeline to Crandell Theatre, Columbia County’s oldest and largest single-screen movie theater. Since being added to the National and State Registers of Historic Places in 2017, it hasn’t stopped showing its top-tier selection of first-run films for locals.

When it comes to a full-on experience, however, Performance Spaces for the 21st Century (PS21) is the place to be. During each season, the cultural center curates a diverse selection of contemporary music, dance, and workshop-driven events. Performers arrive from across the nation and around the globe to showcase their talents in breathtaking spectacles just for the Hudson Valley.


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Balls of IG!! Mac & Cheese balls in a spicy tomato sauce!! #wegotyourballs #ourballsarebadass

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6:30 p.m. – Indulge your inner gourmand at The People’s Pub

Don’t let the name fool you. The People’s Pub is less of a beer-slinging tavern and more of an ultra-cool community restaurant with a killer menu and top-shelf bar program. If it sounds like a dream come true, that’s because it kind of is. After all, where else can you start the night with a cocktail (how about The Old Chatham with bourbon and fresh muddled orange?) and flash-fried Brussels sprouts with honey sriracha glaze, then dive into bibimbap with a perfectly poached egg or handmade pappardelle with seared shrimp?

More of a beer or wine drinker? The People’s Pub stocks a thoughtful selection of brews, bubbles, and vino as well.

8 p.m. – Sip a local pint at Chatham Brewing

Beer might not be the traditional route when it comes to nightcaps, but the drinks at Chatham Brewing might make you reconsider. Make a detour to the taproom after dinner for an on-tap selection that shines a light on Hudson Valley beer culture. You can’t go wrong with anything, but Chatham’s Blood Orange Gose, a simple sour with blood orange puree, and Farmer’s Daughter, a sassy IPA with locally grown rye, hit the spot in the best way.
59 Main St, Chatham
Mon 4-9 p.m., Weds and Sun 12-9 p.m., Thurs 12-10 p.m., Fri-Sat 12 p.m. – 12 a.m.

9 p.m. – Rest your eyes at the Inn at Silver Maple Farm

Just a short drive away from Chatham proper, the Inn at Silver Maple Farm brings new meaning to the notion of escape in East Chatham. Check into the Shaker-inspired inn, which resides on a sprawling property dotted with maple trees, then retreat to one of the 11 guest rooms and suites to relax Hudson Valley-style (if you’re in one of the suites, that means unwinding in the soaking tub or curling up with a book by the gas fireplace). By the time morning rolls around, you’ll be ready to dig into a complimentary breakfast with a surprise second course that could be anything from blueberry buttermilk pancakes to Silver Maple’s signature frittata.
1871 Rte 295, East Chatham

Did we miss a spot? Let us know where to go to find the best of Chatham in the comments or by email at edit@hvmag.com.

Related: What to Eat and Where to Go for a Perfect Day in Red Hook