Our Chatham: A Guidebook

Magaly
Our Chatham: A Guidebook

Food Scene

Our Daily Bread is our favorite breakfast and brunch spot in town. In addition to a pleasant indoor/outdoor dining experience, they have a deli with fresh baked breads and soups for on-the-go dining!
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Our Daily Bread Deli
116 Hudson Avenue
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Our Daily Bread is our favorite breakfast and brunch spot in town. In addition to a pleasant indoor/outdoor dining experience, they have a deli with fresh baked breads and soups for on-the-go dining!
Bimi's Cheese Shop is an artisinal cheese and fixing's shop that is as decadent as it sounds. Stop by and pick up a flaky baguette, a block of fresh local cheese, and a fruity spread for the perfect appetizer. They also make grilled cheese sandwiches, so be sure to check it out for lunch!
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Bimi's Cheese Shop
21 Main St
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Bimi's Cheese Shop is an artisinal cheese and fixing's shop that is as decadent as it sounds. Stop by and pick up a flaky baguette, a block of fresh local cheese, and a fruity spread for the perfect appetizer. They also make grilled cheese sandwiches, so be sure to check it out for lunch!
This is a great spot in town for lunch or dinner and a freshly brewed pint. They offer flights of beer, as well, if you can't decide on which brew to choose. The Brewery occasionally has live music, too!
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Chatham Brewing
59 Main Street
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This is a great spot in town for lunch or dinner and a freshly brewed pint. They offer flights of beer, as well, if you can't decide on which brew to choose. The Brewery occasionally has live music, too!
The Kinderhook Farm is about a 10-minute drive from the Berkshire Chalet. You can't dine in here, but you can explore their shop for locally grown meats and eggs, especially if you value quality provisions and creating farm-to-table meals.
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Kinderhook Farm
1958 County Road 21
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The Kinderhook Farm is about a 10-minute drive from the Berkshire Chalet. You can't dine in here, but you can explore their shop for locally grown meats and eggs, especially if you value quality provisions and creating farm-to-table meals.
The People's Pub is a farm-to-table restaurant located on Main Street in Chatham, NY. This cozy restaurant not only serves delicious, locally sourced meals, but the kitchen is open-concept, so you can see the chefs at work!
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The People's Pub
36 Main Street
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The People's Pub is a farm-to-table restaurant located on Main Street in Chatham, NY. This cozy restaurant not only serves delicious, locally sourced meals, but the kitchen is open-concept, so you can see the chefs at work!
The Blue Plate is a classy American Bistro that provides a fresh take on classic bistro dishes, with such favorites as 'Coq au Vin' and 'Mushroom Risotto.' Sit at the bar downstairs for a cocktail as you wait for your table. Enjoy the experience of fine dining that won't break the bank in the heart of quaint and cozy Chatham, NY.
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Blue Plate
1 Kinderhook Street
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The Blue Plate is a classy American Bistro that provides a fresh take on classic bistro dishes, with such favorites as 'Coq au Vin' and 'Mushroom Risotto.' Sit at the bar downstairs for a cocktail as you wait for your table. Enjoy the experience of fine dining that won't break the bank in the heart of quaint and cozy Chatham, NY.
Nonne is a charming Italian restaurant right in town on Main Street. Their menu is filled with southern Italian cuisine options, including brick-oven pizza, pasta dishes, and main entrees. Our favorite appetizer to order is the canotto: warm focaccia bread fresh from the oven! Visit this spot for an elegant and upscale ambiance with affordable prices.
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nonne
10 Main Street
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Nonne is a charming Italian restaurant right in town on Main Street. Their menu is filled with southern Italian cuisine options, including brick-oven pizza, pasta dishes, and main entrees. Our favorite appetizer to order is the canotto: warm focaccia bread fresh from the oven! Visit this spot for an elegant and upscale ambiance with affordable prices.
Fiesta Cafe serves tasty Mexican food right in the heart of Chatham, NY. The menu is extensive and delicious! Choose from tacos, empanadas, fajitas, and many other Mexican specialties in between. The churros and Mexican hot chocolate are our favorite desserts!
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Fiesta Cafe
41 Main Street
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Fiesta Cafe serves tasty Mexican food right in the heart of Chatham, NY. The menu is extensive and delicious! Choose from tacos, empanadas, fajitas, and many other Mexican specialties in between. The churros and Mexican hot chocolate are our favorite desserts!
Lagonia's Bistro on Hudson Ave in town is a great spot for lunch and dinner. They have a lengthy and varied menu of Italian food. Come visit to dine indoors, outdoors or order takeout!
Lagonias Bistro
15 Hudson Avenue
Lagonia's Bistro on Hudson Ave in town is a great spot for lunch and dinner. They have a lengthy and varied menu of Italian food. Come visit to dine indoors, outdoors or order takeout!
When our local breakfast spot in Chatham, NY is closed, we always take a 25 minute ride to Main Street Cafe in Stockbridge, MA. Come here to slow down and enjoy a hearty breakfast or lunch that tastes like real home cooking. After your meal, take a walk and browse the numerous gift shops, art galleries or musical events happening in town! Stockbridge, MA is the epitome of Berkshire comfort and culture.
Main Street Cafe
40 Main St
When our local breakfast spot in Chatham, NY is closed, we always take a 25 minute ride to Main Street Cafe in Stockbridge, MA. Come here to slow down and enjoy a hearty breakfast or lunch that tastes like real home cooking. After your meal, take a walk and browse the numerous gift shops, art galleries or musical events happening in town! Stockbridge, MA is the epitome of Berkshire comfort and culture.
Visit No. Six Depot in West Stockbridge, MA for lunch and a cup of coffee. This place serves sandwiches, soups and salads, all with a side of fresh, soft bread; they have vegetarian and vegan options too! Pick up some freshly roasted coffee beans before you go. Both indoor and outdoor dining available.
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No. Six Depot Roastery & Cafe
6 Depot Street
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Visit No. Six Depot in West Stockbridge, MA for lunch and a cup of coffee. This place serves sandwiches, soups and salads, all with a side of fresh, soft bread; they have vegetarian and vegan options too! Pick up some freshly roasted coffee beans before you go. Both indoor and outdoor dining available.
This historic railroad hotel was converted to the uniquely styled cafe pictured here. Great spot for excellent coffee and a light sandwich or pastry. Stay a while and read while you enjoy your beverage, or take it all to go. Highly recommended!
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Bartlett House
2258 NY-66
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This historic railroad hotel was converted to the uniquely styled cafe pictured here. Great spot for excellent coffee and a light sandwich or pastry. Stay a while and read while you enjoy your beverage, or take it all to go. Highly recommended!
This traveling taco truck is parked in Chatham and is worth a visit. Situated inside a greenhouse, Tacos Diablo lets you customize your tacos and either eat inside the light-drenched greenhouse, or take them to go. As a bonus, walk to the cidery across the way, order a drink, and sip it while you eat tacos in the greenhouse. They're currently parked at: 2309 New York 203 Chatham, NY 12037 Call ahead to confirm location.
Tacos Diablo
1.5 Kinderhook Street
This traveling taco truck is parked in Chatham and is worth a visit. Situated inside a greenhouse, Tacos Diablo lets you customize your tacos and either eat inside the light-drenched greenhouse, or take them to go. As a bonus, walk to the cidery across the way, order a drink, and sip it while you eat tacos in the greenhouse. They're currently parked at: 2309 New York 203 Chatham, NY 12037 Call ahead to confirm location.

Recreational Activities

Massachusetts is a 20-30 minute drive away from our home in Chatham, NY. This clean and efficient dispensary is staffed by professionals who approachable and knowledgeable.
Theory Wellness: Recreational and Medical Marijuana Dispensary MA
394 Stockbridge Rd
Massachusetts is a 20-30 minute drive away from our home in Chatham, NY. This clean and efficient dispensary is staffed by professionals who approachable and knowledgeable.
Catamount Mountain Resort is a short 30 minute drive from the chalet in Chatham, NY. Not only is this place a well-known ski destination for the entire family, but it has plenty of outdoor summer activities too, including zip lining, whitewater rafting and an aerial adventure park!
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Catamount Ski Area
78 Catamount Road
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Catamount Mountain Resort is a short 30 minute drive from the chalet in Chatham, NY. Not only is this place a well-known ski destination for the entire family, but it has plenty of outdoor summer activities too, including zip lining, whitewater rafting and an aerial adventure park!
Jiminy Peak Mountain Resort is the place for all-season, outdoor fun - and it's only a quick 35 minute drive from the Chalet in Chatham, NY! Not only does this resort have skiing/snowboarding (and lessons) for all ages and abilities, but adventurers can also enjoy other outdoor winter activities, such as snowshoeing and hiking. Guests can also enjoy the day spa and several art and historical museums. The summer season is just as exciting as the winter, as Jiminy Peak offers an exhaustive list of outdoor activities for the entire family. Enjoy a mountain coaster, an alpine super slide, zip lining, rock climbing, trampolines, mountain biking, an aerial adventure park and miles of hiking trails. They also host a Halloween Festival in October, for travelers that like to be spooked.
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Jiminy Peak
37 Corey Road
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Jiminy Peak Mountain Resort is the place for all-season, outdoor fun - and it's only a quick 35 minute drive from the Chalet in Chatham, NY! Not only does this resort have skiing/snowboarding (and lessons) for all ages and abilities, but adventurers can also enjoy other outdoor winter activities, such as snowshoeing and hiking. Guests can also enjoy the day spa and several art and historical museums. The summer season is just as exciting as the winter, as Jiminy Peak offers an exhaustive list of outdoor activities for the entire family. Enjoy a mountain coaster, an alpine super slide, zip lining, rock climbing, trampolines, mountain biking, an aerial adventure park and miles of hiking trails. They also host a Halloween Festival in October, for travelers that like to be spooked.
The Columbia County Fair is a traditional county fair that takes place every fall in the heart of Chatham, NY. Vendors of the County Fair promote agriculture, horticulture and arts and crafts for all age groups through educational instructions, displays and competitions. Enjoy a corndog, ride the ferris wheel, meet farm animals and make some memories!
Columbia County Fair Grounds
182 Hudson Ave
The Columbia County Fair is a traditional county fair that takes place every fall in the heart of Chatham, NY. Vendors of the County Fair promote agriculture, horticulture and arts and crafts for all age groups through educational instructions, displays and competitions. Enjoy a corndog, ride the ferris wheel, meet farm animals and make some memories!
People traveling with kids will love this local spot, a short 10 minute drive from the Chalet. It has a swimming hole, a small skate park, a play ground, picnic grounds and lots of open space to run around. Visit their website for more activities: www.chathamnewyork.us/departments/recreation_department.php
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Crellin Park
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People traveling with kids will love this local spot, a short 10 minute drive from the Chalet. It has a swimming hole, a small skate park, a play ground, picnic grounds and lots of open space to run around. Visit their website for more activities: www.chathamnewyork.us/departments/recreation_department.php
Visit this quaint yet modern winery just outside of Chatham in Ghent, about a 10-minute drive from the house. Grab a glass of your favorite white, red, rose or sparkling wine and sit by a fire pit outside overlooking the vineyard. Or, come with a group, order a charcuterie board and enjoy their wine tasting for $18 per person. The owners are knowledgeable, friendly and down-to-earth.
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Hudson Chatham Winery
1900 New York 66
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Visit this quaint yet modern winery just outside of Chatham in Ghent, about a 10-minute drive from the house. Grab a glass of your favorite white, red, rose or sparkling wine and sit by a fire pit outside overlooking the vineyard. Or, come with a group, order a charcuterie board and enjoy their wine tasting for $18 per person. The owners are knowledgeable, friendly and down-to-earth.

The Arts

The Tanglewood Music Festival is a music festival held every summer in Lenox, MA, in the heart of the Berkshires. The festival consists of a series of concerts, including symphonic music, chamber music, choral music, musical theater, contemporary music, jazz, and pop music. It's also home to the Boston Symphony Orchestra, though they share the stage with many other musicians. This prestigious music festival is one of the top in the world. Remote concerts are available to attend during the COVID-19 pandemic.
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Tanglewood
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The Tanglewood Music Festival is a music festival held every summer in Lenox, MA, in the heart of the Berkshires. The festival consists of a series of concerts, including symphonic music, chamber music, choral music, musical theater, contemporary music, jazz, and pop music. It's also home to the Boston Symphony Orchestra, though they share the stage with many other musicians. This prestigious music festival is one of the top in the world. Remote concerts are available to attend during the COVID-19 pandemic.
The Crandell Theatre is a historic staple of Chatham's Main Street and home to the Columbia County Film Festival.
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Crandell Theatre
48 Main Street
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The Crandell Theatre is a historic staple of Chatham's Main Street and home to the Columbia County Film Festival.
Tannery Pond Concerts presents chamber music in the heart of the scenic Berkshires during May through September. https://tannery-pond-concerts.myshopify.com/
Tannery Pond
Tannery Pond Concerts presents chamber music in the heart of the scenic Berkshires during May through September. https://tannery-pond-concerts.myshopify.com/
The Midnight Ramble is a weekly concert series that takes place in the timber-frame home of the recently deceased rock legend, Levon Helm. You may know Levon as the drummer from The Band, the Canadian-American rock group formed in the late '60s. This venue hosts a wide range of well-known and up-and-coming artists from a splattering of musical genres, including country, rock, folk, jazz, blues, and even rockabily! The Midnight Ramble is an hour drive from the Berkshire Chalet.
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Levon Helm Studios
160 Plochmann Lane
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The Midnight Ramble is a weekly concert series that takes place in the timber-frame home of the recently deceased rock legend, Levon Helm. You may know Levon as the drummer from The Band, the Canadian-American rock group formed in the late '60s. This venue hosts a wide range of well-known and up-and-coming artists from a splattering of musical genres, including country, rock, folk, jazz, blues, and even rockabily! The Midnight Ramble is an hour drive from the Berkshire Chalet.

Neighborhoods

Lenox, MA is a brief, 30-minute drive from the Berkshire Chalet. We have loved shopping and antiquing in Lenox over the years! There is much more to do here, however. For more ideas, follow the link below: https://lenox.org/category/things-to-do/
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Lenox
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Lenox, MA is a brief, 30-minute drive from the Berkshire Chalet. We have loved shopping and antiquing in Lenox over the years! There is much more to do here, however. For more ideas, follow the link below: https://lenox.org/category/things-to-do/
Hudson, NY is a trendy town in the Hudson Valley of New York and is only a quick 25 minute drive from the Berkshire Chalet. This town is situated on the banks of the picturesque Hudson River and is becoming known for it's fine dining and collection of art galleries. Grab a coffee in town, browse the art galleries, shop the boutiques, stop for a leisurely lunch in town, then enjoy an ice cream by the water! This is also one of the closest locations to the Air BnB with larger businesses; if you can't find a service or store in Chatham, NY, you will likely have luck if you drive to Hudson.
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Hudson
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Hudson, NY is a trendy town in the Hudson Valley of New York and is only a quick 25 minute drive from the Berkshire Chalet. This town is situated on the banks of the picturesque Hudson River and is becoming known for it's fine dining and collection of art galleries. Grab a coffee in town, browse the art galleries, shop the boutiques, stop for a leisurely lunch in town, then enjoy an ice cream by the water! This is also one of the closest locations to the Air BnB with larger businesses; if you can't find a service or store in Chatham, NY, you will likely have luck if you drive to Hudson.
Stockbridge, MA is a quaint and picturesque town about 25 minutes east of the Air BnB. Take a day trip here for great eats, boutiques, antiques and many arts and cultural activities. This town has plenty of arts and cultural activities for the whole family and is a must-visit if you're looking for an eventful day outside of the Air BnB house. Stockbridge is the epitome of Berkshire style, culture and comfort.
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Stockbridge
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Stockbridge, MA is a quaint and picturesque town about 25 minutes east of the Air BnB. Take a day trip here for great eats, boutiques, antiques and many arts and cultural activities. This town has plenty of arts and cultural activities for the whole family and is a must-visit if you're looking for an eventful day outside of the Air BnB house. Stockbridge is the epitome of Berkshire style, culture and comfort.

Groceries & Sundries

This is the main supermarket in town; it has a pharmacy inside, too.
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Price Chopper
2614 New York 66
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This is the main supermarket in town; it has a pharmacy inside, too.
Lovely wine and liquor store near the Price Chopper supermarket. Excellent selection!
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(drink.)
15 Dardess Dr
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Lovely wine and liquor store near the Price Chopper supermarket. Excellent selection!
Quaint wine and liquor store right in town on Main Street, Chatham, NY. Lots of options!
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Chatham Wine & Liquor
53 Main St
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Quaint wine and liquor store right in town on Main Street, Chatham, NY. Lots of options!
There's a Walgreens in town for sundries and snacks.
Walgreens
15 Coleman Street
There's a Walgreens in town for sundries and snacks.
The Kinderhook Farm is about a 10-minute drive from the Berkshire Chalet. You can't dine in here, but you can explore their shop for locally grown meats and eggs, especially if you value quality provisions and creating farm-to-table meals.
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Kinderhook Farm
1958 County Road 21
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The Kinderhook Farm is about a 10-minute drive from the Berkshire Chalet. You can't dine in here, but you can explore their shop for locally grown meats and eggs, especially if you value quality provisions and creating farm-to-table meals.
If you're looking to cook a farm-to-table style meal, stop by Grimaldi Farms for local fare. This local farm store sells meat, poultry and eggs.
Grimaldi Farm Store - Certified Organic Grass-Fed Beef
22 Old Talerico Road
If you're looking to cook a farm-to-table style meal, stop by Grimaldi Farms for local fare. This local farm store sells meat, poultry and eggs.
This local farm market has it all: meats and produce; artisanal jams, oils and spreads; custom made wreaths; unique plants; gifts and trinkets; local honey - you name it!
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The Chatham Berry Farm LLC
2309 State Route 203
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This local farm market has it all: meats and produce; artisanal jams, oils and spreads; custom made wreaths; unique plants; gifts and trinkets; local honey - you name it!