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Hudson Valley Art, Estates & Heritage Road Journey: 3-Day Plan You Can Actually Drive

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The 3-day version for October: every day fits real transit, opening hours and daylight. Prefer more or fewer days? 3-day plan · 4-day plan · best time to go.

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3
days
160 km
distance
3.9 h
driving
15
curated stops

💡 Good to know for this plan

Before you go · check live details

This is a planning draft. Check these changing details for your dates before booking or travelling.

Day 1 Tarrytown & Sleepy Hollow

6 curated stops
Transit
0h47
Finish
~17:25
Temperature
8.1°C–17.8°C
Rainy days
~17
Daylight
10.9h
09:00
Tarrytown and Sleepy Hollow public heritage circuit hudsonvalley.org map ↗
Use public town and heritage sites subject to current timed estate access.
50 min · Tarrytown & Sleepy Hollow · Public areas; confirm current admission and opening before entry
10:00
Andre Captor’s Monument search map ↗
Stand at the historic spot where the spy John André was captured during the Revolutionary War.
50 min · Tarrytown & Sleepy Hollow
11:05
Lyndhurst lyndhurst.org read more map ↗
Wander through the grand Gothic mansion and enjoy sweeping views of the Hudson Valley.
50 min · Tarrytown & Sleepy Hollow · Mansion: adults $10, seniors $9, students 12-17 with adult $4, children under 12 with adult free. Grounds only: $4.
open: Mid-April through October, Tue-Sun and holiday Mondays, 10AM-5PM. November through mid-April, Sat and Sun only, 10AM-4PM
12:05
Sunnyside hudsonvalley.org read more map ↗
Stroll the lush gardens and take in breathtaking vistas of the Hudson River.
50 min · Tarrytown & Sleepy Hollow · adult $12, seniors 65+ $10, children 3-17 $6
open: Admission by timed tours only. May 3-Nov 12, Wed-Sun. Also open Memorial Day, July 3 and 4, Labor Day, and Columbus Day. Weekdays: 10:30AM, 11, 11:30, 12:30PM, 1:30, 2, 2:30, 3, 3:30. Weekends and holidays: Every half hour. First tour 10am, last tour 3:30PM. Additional tour at 4PM, May 27 through September 4.. Allow approximately one hour to visit.
13:10
Follow Ichabod Crane's flight from the Headless Horseman sleepyhollowcemetery.org
Trace the legendary path from Tarrytown to Sleepy Hollow as you imagine Ichabod's escape.
90 min · Tarrytown & Sleepy Hollow
14:55
Visit the farmers market tashfarmersmarket.org
Browse fresh Hudson Valley produce, meats, and bread, with occasional live music and crafts.
90 min · Tarrytown & Sleepy Hollow
16:25
Taste of China toctarrytown.com map ↗
Enjoy vegetarian Chinese fare, either eaten in or taken out for a quick meal.
60 min · Tarrytown & Sleepy Hollow · Lunch specials start around $5, dinners start around $10
open: Sun–Thu 10:30AM–10:45PM, Fri Sat 10:30AM–11:45PM
Overnight here
e.g. Castle Hotel and Spa · Courtyard Tarrytown Westchester County
Find a stay → Tours & tickets for the evening →

Day 2 Beacon

3 curated stops
Transit
1h37
Finish
~13:15
Temperature
6.2°C–16.9°C
Rainy days
~18
Daylight
10.9h
10:25
Beacon and New Paltz public art-and-history circuit diaart.org map ↗
Use Dia Beacon and public New Paltz history; specialist outdoor activities remain separate.
50 min · Beacon · Public areas; confirm current admission and opening before entry
11:25
Dia:Beacon diaart.org read more map ↗
Explore modern art in a vast, repurposed factory with stunning riverfront views.
50 min · Beacon · Adults $20, seniors $18, students $12, children 5-11 $5. Free admission for Dia members
open: January–March: Fri–Mon 10AM–4PM; April–October: Thu-Mon 11AM–6PM; November–December: Thu-Mon 11AM–4PM
12:25
Mount Gulian Historical Site mountgulian.org map ↗
Discover the rich history of the Verplanck family in a beautiful, story-filled setting.
50 min · Beacon · Adults $8, seniors $6, children (age 6-18) $4. Free admission for Mount Gulian members
open: May–Oct: Wed–Fri Sun 1–5PM, last tour at 4PM
Overnight here
e.g. Swann Inn of Beacon
Find a stay → Tours & tickets for the evening →

Day 3 Rhinebeck

4 curated stops
Transit
1h32
Finish
~15:05
Temperature
5.1°C–16.1°C
Rainy days
~18
Daylight
10.8h
10:00
Rhinebeck public heritage circuit parks.ny.gov map ↗
Use public Rhinebeck heritage subject to current museum and estate opening.
50 min · Rhinebeck · Public areas; confirm current admission and opening before entry
11:05
Rhinebeck Post Office tools.usps.com
Admire WPA-era murals and historic architecture.
50 min · Rhinebeck
open: Mon-Fri: 9:00AM-5:00PM, Sat: 9:00AM-3:00PM, Sun: closed
12:10
Old Rhinebeck Aerodrome oldrhinebeck.org
Witness airworthy vintage aircraft taking flight.
50 min · Rhinebeck
13:15
Wilderstein wilderstein.org
Explore a stunning mansion in beautiful park-like grounds.
50 min · Rhinebeck
14:05
Aba's Falafel abasfalafel.com
Delight in fresh, flavorful falafel and sabich.
60 min · Rhinebeck · Sandwiches: $10.75-12.75; platters: $17-18
open: Daily 11AM-3:30PM

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🔍 Check before you book

Every stop is a real, sourced place, but opening hours change, roads close and businesses move. Check anything you're paying for before you book.

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