Fall Foliage Train Adventure: Upstate New York from NYC

Day 1: Hudson Valley Heights

New York City, USA

8:00AM

Breakfast at The Grey Dog

Start your day with a hearty breakfast of their famous avocado toast and a craft coffee to fuel up for your journey ahead.
Walk to Penn Station.
USD15, 1 hour

9:30AM

Train to Poughkeepsie

Board the Amtrak train to Poughkeepsie, enjoying the scenic views of the Hudson River as the train winds northward.
Take the Amtrak train from Penn Station.
USD35, 1 hour 45 minutes

11:15AM

Explore Walkway Over the Hudson

Once you arrive in Poughkeepsie, take a leisurely stroll across this historic railroad bridge that offers stunning views of the Hudson River and surrounding fall colors.
Take a short taxi from the station to the Walkway.
Free, 1 hour

12:30PM

Lunch at The Pasta Factory

Sit down for a delicious lunch featuring homemade pasta dishes complemented by local herbs and vegetables.
Taxi back to Poughkeepsie.
USD20, 1 hour

2:00PM

Train to Rhinebeck

Catch a local train or taxi to Rhinebeck, a charming village known for its beautiful architecture and autumn ambiance.
Take a quick train or taxi ride to Rhinebeck.
USD10, 30 minutes

3:00PM

Visit the Rhinebeck Antique Emporium

Spend some time browsing through various vintage treasures and antiques in the heart of Rhinebeck.
Walk around the town center.
Free, 1 hour

4:30PM

Enjoy Rhinebeck Waterfront Park

Take a relaxing walk at the Rhinebeck Waterfront Park, watching the river and absorbing the stunning fall foliage.
Walk to the park from the Emporium.
Free, 1 hour

6:00PM

Dinner at The Beekman Arms

Dine at New York State's oldest inn, savoring classic American fare in a cozy and historic setting.
Walk back to the inn.
USD50, 1.5 hours

8:00PM

Check into Local Inn

Unwind at a lovely local inn before preparing for the adventure-filled day ahead.
Stay at the inn you checked into.
USD150, N/A
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Day 2: Catskills Exploration

Catskills, NY, USA

8:30AM

Breakfast at The Rhinecliff

Enjoy a delightful breakfast with a view of the river; try their fluffy pancakes topped with seasonal fruits.
Walk to The Rhinecliff.
USD25, 1 hour

9:30AM

Travel to Catskill Mountains

Drive or take a guided tour to the Catskill Mountain range for stunning views and fall foliage.
Rent a car or join a guided tour.
USD80 (car rental for the day), 1 hour

10:30AM

Hiking at Kaaterskill Falls

Embark on a short hike to see Kaaterskill Falls, one of New York's tallest waterfalls, surrounded by vibrant fall colors.
Park and hike the designated trails.
Free, 2 hours

12:30PM

Lunch at The Catskill Mountain House

Savor a farm-to-table lunch with an emphasis on local ingredients, wrapped in a beautiful mountain atmosphere.
Drive to the Catskill Mountain House.
USD35, 1.5 hours

2:00PM

Visit the Olana State Historic Site

Explore the historic home of Frederic Edwin Church, a leading figure in the Hudson River School art movement, along with stunning grounds.
Drive to Olana.
USD10, 2 hours

4:30PM

Wander Around Woodstock

Travel to the iconic Woodstock, a haven for artists, and explore its unique shops and art galleries.
Drive to Woodstock.
Free, 1.5 hours

6:00PM

Dinner at The Bear Cafe

Feast on delicious locally-sourced dishes while admiring the scenic views at this beloved spot
Walk to the restaurant.
USD40, 2 hours

8:30PM

Return to Inn

Head back to your inn for a restful night after a full day of exploration.
Drive back to your inn.
N/A, 1 hour
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Day 3: Mountain Retreat and Return

New Paltz, NY, USA

8:30AM

Breakfast at The Bakery

Begin your day with fresh pastries and locally brewed coffee, soaking in the cozy ambiance of this popular spot.
Walk to The Bakery.
USD15, 1 hour

9:30AM

Visit Mohonk Preserve

Explore the breathtaking landscapes and trails at Mohonk Preserve, where nature and vibrant fall colors meet.
Drive to Mohonk Preserve entrance.
USD20, 2.5 hours

12:00PM

Lunch at The Mountain House

Enjoy a scenic overlook lunch at The Mountain House, where you can soak in views of the mountains while indulging in a light meal.
Lunch on-site at Mohonk.
USD30, 1 hour

1:30PM

Bear Mountain State Park

Continue on for a visit to Bear Mountain State Park, perfect for more stunning scenery and a leisurely walk along the trails.
Drive to Bear Mountain.
USD10, 2 hours

3:30PM

Head Back to NYC

Wrap up your trip by starting your return journey back to New York City, reflecting on the idyllic fall experience you’ve had.
Drive back to Poughkeepsie for your train.
USD35 (for train ticket), 1 hour

5:30PM

Train Back to NYC

Board the Amtrak train to return to the hustle and bustle of New York City.
Catch the train from Poughkeepsie to Penn Station.
USD35, 1 hour 45 minutes

7:15PM

Dinner at Penn Station

Conclude your trip with a light dinner at the station's food court, where you can grab a quick bite before heading home.
Eat at the food court.
USD20, 1 hour
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