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Top Ten Ways to See Dutchess County

There are many ways to take in the sights of beautiful Dutchess, in heart of the Hudson Valley, via all manner of transportation! So many, this list actually contains 11!

1. Trains
Take a train right into Dutchess County! Metro-North’s Hudson Line stops in Beacon, New Hamburg, and Poughkeepsie. The Harlem Line goes to Pawling, Appalachian Trail, Harlem Valley-Wingdale, Dover Plains, Ten Mile River and Wassaic. Check out Metro-North’s One-Day Get Away packages to various sites in Dutchess County including our fall Farm Fresh tours! Amtrak also stops in Poughkeepsie and Rhinecliff.

2. Planes
Flying to the Hudson Valley is easy, whether you're flying from a few states or an ocean away! With a county, nearby international, and a small privately owned airport open to the public, we're only a plane ride away.
Hudson Valley Regional Airport, Wappingers Falls
Stewart International Airport (SWF), Newburgh
Sky Acres Airport, Lagrangeville

3. Walking
Take Dutchess County in at your leisure! Your own two feet will get you to some of the best places in the Hudson Valley.

  • The Museum in the Streets© of Millbrook is a self-guided walking tour, featuring 31 permanent plaques, designed to promote a sense of historical identity and encourage the preservation of local history.
  • Head out from the Beacon Train station and discover Long Dock Park along the Hudson River, Dennings Point, the site of a former important brickyard, Main Street with the shops and art galleries, and hike up Mount Beacon along the incline railroad trail.
  • Walk around Tivoli & Red Hook with a guide, and learn the history of both villages.
  • And of course don't forget the Walkway Over the Hudson, 212' above the Hudson River and 1.25 miles long!

4. Biking
Green, healthy, and fun, biking is always a great choice!

  • Bike or walk along several scenic trails in Rhinebeck and Red Hook
  • Follow the 13 mile, multi-use Dutchess County Rail Trail. Stretching between Hopewell Junction and the Walkway over the Hudson, this trail has convenient parking at various locations along the route. On the eastern side of the county lies the Harlem Valley Rail Trail. Weaving through farmland, forests and village centers, this 10 mile trail runs from Wassaic to Millerton. Discover more about these two rail trails here.
  • Finally, enjoy these self-guided bike tours of various spots in Dutchess County. If biking is new to you, try renting one!

5. Boating
There are many ways to see the Hudson River from the land, but few ways to see the Hudson Valley quite like you do from the water. Take the speedy water taxi Shadows One from Shadows Marina and travel between Newburgh and Poughkeepsie in twenty minutes!

Enjoy a boat ride and visit a castle located on an island in the Hudson River! Board the Estuary Steward in Beacon and cruise to Pollepel Island to visit Bannerman’s Castle. Guided and self-guided tours are available, along with special evening constellation tours and live performances.

If you’re more into sailing, try one of these great options: Tivoli Sailing, Black Swan Sailing or Ophira Sailing.

6. Cars
Nothing is more American than cars and there are plenty of places to go! Enjoy these self-guided scenic car tours through the beautiful Hudson Valley. No car? No problem – Zipcars are here. Find them in Beacon, Poughkeepsie, Hyde Park & Annandale-on-Hudson.

Do you enjoy car shows? There are many scheduled throughout the summer and fall including the Hudson River Valley Antique Auto Association's Car show is the first weekend in May at the Dutchess County Fairgrounds, Rhinebeck and in June the Good Guys Rod & Custom Car Show.

7. Buses
Save on gas - take Dutchess County Transit into Hyde Park, Rhinebeck, and other cultural and scenic gems of Dutchess County; just sit back and enjoy the ride! 

8. Horseback Riding
Just you, your guide, a friend or two, and, most importantly, your horse. There’s no better way to enjoy nature than on horseback through some of Dutchess County’s most beautiful countryside.

9. Vintage Airplane
Get a bird's eye view of Dutchess County on the wings of yesteryear. The view from on high at the Old Rhinebeck Aerodrome remains breathtaking. Step back in time as you watch the Barnstorming era or WWI airshows, or get your thrills riding in a 1929 open cockpit biplane.

10. Hot Air Balloon
Soar over the countryside in a hot air balloon! It’s an experience that will be remembered for a lifetime!

11. Trolley
Can’t decide whether to visit Beacon or the Village of Cold Spring? Do BOTH with the Cold Spring to Beacon Trolley. Hop off and on at a wide variety of stops along the way.

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