Best cities in Dutchess County

  • Cities
  • Streets

Red Hook

4/5
Red Hook
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...
42.0151018421863 -73.8934080112464

Hyde Park

4/5
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...
41.7891837411989 -73.8972601092996

Pawling

3.5/5
Pawling
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...
41.5619 -73.6026
Wappingers Falls
Ranked 4th 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...
41.5963850077843 -73.9054151277817

Millerton

3.5/5
Millerton
Ranked 5th 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...
41.9499845521877 -73.5086228809715

LaGrange

3.5/5
LaGrange
Ranked 6th best city in Dutchess County

"LaGrangeville Will Always Hold a Special Place in My Heart"

- SaraKaplan
Located right off the Taconic Parkway in Dutchess County, LaGrange (or LaGrangeville) is a beautiful, family-friendly town that was once populated largely by farmland (as was most of the Hudson Valley...
41.6737873644601 -73.7131630687065
East Fishkill
Ranked 7th best city in Dutchess County

"Growing township with recreational opportunities."

- Kerry Barger
East Fishkill is one of the southern most towns in Dutchess County and runs adjacent to the northern border of Putnam County. Three major roadways, Route 52, the Taconic State Parkway and Interstate 8...
41.5815518747204 -73.7929663266049
Hopewell Junction
Ranked 8th 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...
41.5832893964141 -73.80286702599
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...
41.6832589302669 -73.8857475044052
Stormville
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...
41.5461740040529 -73.7261767799203

Stanford

3/5
Stanford
Ranked 11th best city in Dutchess County

"Hike Stissing Mountain and Smell the Flowers at Buttercup Sa..."

- SaraKaplan
There's so many great things to do in the town of Stanford, NY (not to be confused with Stamford, CT). It's near a beautiful mountain (Stissing Mountain) for which one of its hamlets are named for....
41.9031523369718 -73.6989184011096
Dover Plains
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...
41.74093 -73.57651

Beacon

2.5/5
Beacon
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...
41.5025504303105 -73.9802022303354

Unranked Cities

Fishkill

3.5/5
Fishkill

"Make a Splash in Lovely Fishkill---where "Kill" Just Means "..."

- SaraKaplan
Fishkill, in spite of its name, is a friendly place that doesn’t want to kill fish. There was even a dispute with the mayor regarding the name, which actually means “fish” and “stream”, as “kill” is t...
41.5339078170169 -73.893802278777

Millbrook

3.5/5
Millbrook

"A village with wealth and character"

- Anjanette
Millbrook is a lovely little 1.9 square mile village in the center of the greater town of Washington, NY in Dutchess County. It is quite affluent and is sometimes compared to the Hamptons in Long Isl...
41.8081248510179 -73.644205686641
Pine Plains

"Amazing Views of Stissing Mountain in a Cozy Country Town"

- SaraKaplan
Pine Plains, located at the crossroads of Rts. 199 and 82, is a great place to visit as well as live in. As most homes only cost a fair $165,000, the town's cost of living is very reasonable. You ge...
41.9784165725816 -73.6575179833448
Pleasant Valley

"It's...well....Pleasant!"

- SaraKaplan
Pleasant Valley, Dutchess County is home to James Baird State Park, 590 acres of park that includes an 18 hole golf course, trails throughout the wooded areas, picnic tables and pavilions, a nature ce...
41.7473754408017 -73.8156505116319

Rhinebeck

3.5/5
Rhinebeck

"Take a Trip Down Memory Lane, and Find a Treasure in Histori..."

- SaraKaplan
When people think of Rhinebeck, they usually remember visiting the Dutchess County Fair, riding the Ferris wheel or watching a lamb win first place in the 4-H fair. While Rhinebeck is famous for this...
41.93349230879 -73.9111041416632
Staatsburg

"Enjoy a Close-Knit Community and Great River Views"

- SaraKaplan
Straatsburg, the smallest hamlet of historic Hyde Park in Dutchess County, NY, is home ot the beautiful Mills-Norrie State Park, which contains 192 acres , along with the stunning turn-of-the-century...
41.8537803654762 -73.924156939402

Tivoli

4/5
Tivoli

"Visit Tivoli, Red Hook of Rhinebeck's College Town"

- SaraKaplan
Tivoli is your average college town located in the heart of the Hudson River Historic District, residing in the greater town of Rhinebeck, NY. As it’s right near Bard College, Tivoli is known as bein...
42.059614011547 -73.9146221466016
41.7857904928974 -73.7653702585701 4

Best Neighborhoods to Live In

Best Cities to Live In

Tell everyone what you love about your neighborhood!

Leave a Review

Have a question?

How are schools? Is the area safe? What about public transit options?" Why not ask our community of locals!

Ask Now

Selling or Renting Your Home?

Maximize the selling price of your home by sharing what you love about your suburb to increase its appeal...

Leave a Review

Corporate Relocation Manager?

Enable your employees to share local knowledge in a private, trusted environment with those relocating... while building community.

Learn More