Best cities in Dutchess County
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Ranked 1st best city in Dutchess County
"Lovely Creative Shops, Pleasant Folks and Friendly Atmospher..."
- SaraKaplan
Red Hook is a charming village located within the town of Rhinebeck, named after Dutch settlers arrived to see the Fall foliage on a peninsula named Cruger’s Island (peninsula in Dutch is “hoek”, and...
Ranked 2nd best city in Dutchess County
"History Buffs Will Love It, Families will Treasure It, Food..."
- SaraKaplan
Most people know Hyde Park as the hometown of our country’s 32nd president, Franklin D. Roosevelt, and many come to visit the stunningly beautiful Roosevelt estate (known as Springwood). However, Hyde...
Ranked 3rd best city in Dutchess County
"Residential neighborhoods spaced out by natural environment."
- Kerry Barger
Pinched between Interstate 84 and the Connecticut border, Pawling really epitomizes the nature of small-town America. Located at the crossroads of Routes 55 (south) and 22 (north), Pawling is located...
Ranked 4th best city in Dutchess County
"Time Slows Down with a Cup of Tea and a Book in Hand in Mill..."
- SaraKaplan
When visiting a reunion at my summer camp Wa Wa Segowea in the Berkshiers, I would pass through Millerton via Rt. 361. It was always a welcoming site and resting stop when my mom would bring me home f...
Ranked 7th best city in Dutchess County
"A Junction at the Crossroads of Hope and Possibility"
- SaraKaplan
You might not know it passing through, but Hopewell Junction is a small gem amongst the many towns and cities in New York’s Dutchess County. Ranked as Money Magazine’s “31st most desirable place to li...
Ranked 8th best city in Dutchess County
"When Visiting the Falls, Remember the 3 P's: Parks, Pizza an..."
- SaraKaplan
Wappingers Falls (not to be confused with its parent town of Wappinger) is located along NY Rt 9 and shared between the city of Poughkeepsie and town of Wappinger, is a lovely village in Dutchess Coun...
Ranked 9th best city in Dutchess County
"The Town of Poughkeepsie Offers Something for Everyone"
- Arij Kurzum
The town of Poughkeepsie offers a suburban life style while close to all amenities: Shopping malls and plazas, hospitals, colleges, restaurants, health clubs, golfing, culture. The train station is...
Ranked 10th best city in Dutchess County
"Home to One of the World's Greatest, Oldest Flea Markets in..."
- SaraKaplan
Don’t go by its name, because Stormville, NY is actually a very pleasant area. In fact, Stormville is quite a unique town in Dutchess County as it has its very own airport named after itself, as well...
Ranked 12th best city in Dutchess County
"Old England, Meet New England"
- SaraKaplan
Dover is a town in Eastern Dutchess County, NY, just West of Connecticut and near the quaint country towns of Amenia and Pawling of Putnam, NY. It's home to many lovely hamlets like Wingdale and Dove...
Ranked 13th best city in Dutchess County
"Moved to beacon because..."
- MatthewR
Beacon is a small town that sounds like Bacon. It gets you started on a solid foot.
Beacon is walkable and tightly knit. Because it is affordable and rests between mountains and the river it has a...
