Guidebook for Hillsdale
Food Scene
I love this little pub. Simple, delicious grub, and good old American brews on tap. The staff is so friendly. This is a Cheers kind of place.
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Mount Washington House Tavern and Restaurant
2627 NY-23I love this little pub. Simple, delicious grub, and good old American brews on tap. The staff is so friendly. This is a Cheers kind of place.
You can walk here in about 10 minutes, and you'd have a hard time finding better food driving 30 minutes anywhere. The baked goods are excellent (and excellently priced); the coffee flows; and I've yet to order something that didn't rival the best fare from foodie destinations all over the country.
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Crossroads Food Shop
2642 NY-23You can walk here in about 10 minutes, and you'd have a hard time finding better food driving 30 minutes anywhere. The baked goods are excellent (and excellently priced); the coffee flows; and I've yet to order something that didn't rival the best fare from foodie destinations all over the country.
Ranked one of the best restaurants in Massachusetts, this gem of a farm to table restaurant maintains a happy, thoughtful atmosphere even when it's brimming with people — and it often is. Get there early or late to avoid a long wait for a table.
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The Prairie Whale
178 Main StRanked one of the best restaurants in Massachusetts, this gem of a farm to table restaurant maintains a happy, thoughtful atmosphere even when it's brimming with people — and it often is. Get there early or late to avoid a long wait for a table.
Some of the best farm-to-table food in the area, make sure you book your table in advance: Tables fill up just about as soon as it opens.
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Local 111
111 Main StSome of the best farm-to-table food in the area, make sure you book your table in advance: Tables fill up just about as soon as it opens.
Drinks & Nightlife
Great beers, good food (including a lot of veggie options), and the best atmosphere, this dive is a special spot on its own, or as an alternative if Local 111 fills up.
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Main Street Public House
12 Main StGreat beers, good food (including a lot of veggie options), and the best atmosphere, this dive is a special spot on its own, or as an alternative if Local 111 fills up.
Arts & Culture
One of the most unique and fascinating museums in the country, this beautifully restored village transports you back into the point in history that established New England's soul. Go to any or all of the free talks throughout the day, explore the working farm, and grab a bite (or cone) at the Seeds Market Cafe. Heck, even go for a hike. This place is magical.
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Villaggio Hancock Shaker
1843 W Housatonic StOne of the most unique and fascinating museums in the country, this beautifully restored village transports you back into the point in history that established New England's soul. Go to any or all of the free talks throughout the day, explore the working farm, and grab a bite (or cone) at the Seeds Market Cafe. Heck, even go for a hike. This place is magical.
A fascinating architectural monument to one of America's greatest early American authors, make sure you sign up for the tour, and explore the grounds after.
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The Mount, Casa di Edith Wharton
2 Plunkett StA fascinating architectural monument to one of America's greatest early American authors, make sure you sign up for the tour, and explore the grounds after.
A sprawling and gorgeous space, with a rotation of exhibitions that are always interesting, occasionally breathtaking. It's a good excuse to drive through the bulk of the Berkshires.
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MASS MoCA
1040 Mass MoCA WayA sprawling and gorgeous space, with a rotation of exhibitions that are always interesting, occasionally breathtaking. It's a good excuse to drive through the bulk of the Berkshires.
Parks & Nature
A quick drive down the road, this is an easy hike that rewards you the whole way with beautiful forest and a cheerful little creek — streaming from a really impressive waterfall. It used to be a swimming hole until swimming was forbidden, but a lot of people hike in swim trunks anyway (nudge nudge, wink wink).
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Parco Statale Bash Bish Falls
Falls RoadA quick drive down the road, this is an easy hike that rewards you the whole way with beautiful forest and a cheerful little creek — streaming from a really impressive waterfall. It used to be a swimming hole until swimming was forbidden, but a lot of people hike in swim trunks anyway (nudge nudge, wink wink).
For something a little more removed and strenuous, this trail rewards you at the end with an old fire tower that offers some of the best views of the Hudson Valley I've come across. It's remote and quiet, a perfect late afternoon hike to whet your appetite for dinner.
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Beebe Hill State Forest
County Route 5For something a little more removed and strenuous, this trail rewards you at the end with an old fire tower that offers some of the best views of the Hudson Valley I've come across. It's remote and quiet, a perfect late afternoon hike to whet your appetite for dinner.
Allegedly where Herman Melville concocted the basis for Moby Dick, this trail offers a range of difficulties with well-marked (and well-trod) trails. If you're game for it, take the red trail up to the peak. Your legs might burn, but you won't be disappointed.
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Monument Mountain Reservation
Allegedly where Herman Melville concocted the basis for Moby Dick, this trail offers a range of difficulties with well-marked (and well-trod) trails. If you're game for it, take the red trail up to the peak. Your legs might burn, but you won't be disappointed.
Shopping
The best curated shop in the area, these guys have a knack for finding tasteful, beautiful things — old and new. It isn't cheap, but if you want to take home a bit of Hillsdale or find a generous housewarming present, this will be your best bet.
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Hillsdale General Store
2642 NY-23The best curated shop in the area, these guys have a knack for finding tasteful, beautiful things — old and new. It isn't cheap, but if you want to take home a bit of Hillsdale or find a generous housewarming present, this will be your best bet.
This is the local watering hole in Hudson, and for good reason. They curate their books well and keep a great rotating list of local pints and wines.
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Spotty Dog Books & Ale
440 Warren StThis is the local watering hole in Hudson, and for good reason. They curate their books well and keep a great rotating list of local pints and wines.
You will not find a better used bookstore in the area. Maybe, in the country. This place is absolutely magical — and affordable. Find a dozen first editions for a few bucks apiece, and a whole host of tomes on local history if you're interested.
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Rodgers Book Barn
467 Rodman RdYou will not find a better used bookstore in the area. Maybe, in the country. This place is absolutely magical — and affordable. Find a dozen first editions for a few bucks apiece, and a whole host of tomes on local history if you're interested.
You can’t swing a cat in Hudson without hitting five antique stores, but I’ve found Finch’s selection the most interesting and (relatively speaking) affordable.
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FINCH hudson
427 Warren StYou can’t swing a cat in Hudson without hitting five antique stores, but I’ve found Finch’s selection the most interesting and (relatively speaking) affordable.
For more affordable and regional antiques, they have the best prices and largest selection in the area. It’s also a good excuse to explore Millerton, a fabulous little spot.
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Old Mill of Irondale
6082 NY-22For more affordable and regional antiques, they have the best prices and largest selection in the area. It’s also a good excuse to explore Millerton, a fabulous little spot.
Essentials
You wouldn't think it from the outside, but our local IGA has just about every ingredient you could need for any dish. Affordable and close, you can walk there and back easily, depending on the number of six-packs you can carry.
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Hillsdale Supermarket
2628 NY-23You wouldn't think it from the outside, but our local IGA has just about every ingredient you could need for any dish. Affordable and close, you can walk there and back easily, depending on the number of six-packs you can carry.
Entertainment & Activities
A beautifully restored one-screen cinema, their few showtimes offer a great excuse to drive up to and explore Chatham. With shops, bakeries, and taverns steps away, you'll be charmed by this place.
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Crandell Theatre
48 Main StA beautifully restored one-screen cinema, their few showtimes offer a great excuse to drive up to and explore Chatham. With shops, bakeries, and taverns steps away, you'll be charmed by this place.
What a special little theater this is. Curating a beautiful selection of film, American and foreign, old and new, just about every weekend there's something for everyone. After you leave, keep your car parked in the lot and step over to Warren to browse the best of Hudson's (quite costly) antiques.
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Time & Space Limited
434 Columbia StWhat a special little theater this is. Curating a beautiful selection of film, American and foreign, old and new, just about every weekend there's something for everyone. After you leave, keep your car parked in the lot and step over to Warren to browse the best of Hudson's (quite costly) antiques.