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The Hudson Valley: 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? 2-day plan · 3-day plan · 4-day plan · best time to go.
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3
days
160 km
distance
3.6 h
driving
14
curated stops
💡 Good to know for this plan
- ~10.9 hours of daylight in October — the plan keeps days inside a realistic window.
- Leaf season on America's first scenic river — Dia:Beacon's galleries, cider donuts at every farm stand, and Sleepy Hollow doing Halloween as a civic duty.
Day 1 Tarrytown & Sleepy Hollow
- Transit
- 0h47
- Finish
- ~17:25
- Temperature
- 8.1°C–17.8°C
- Rainy days
- ~17
- Daylight
- 10.9h
09:00
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, W-Su. Also open Memorial Day, July 3 and 4, Labor Day, and Columbus Day. Weekdays: 10:30AM, 11, 11:30, 12:30PM, …
10:00
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, Tu-Su and holiday Mondays, 10AM-5PM. November through mid-April, Sa and Su only, 10AM-4PM
11:05
12:05
13:10
Sleepy Hollow Chamber of Commerce search
Find local guides and event listings to plan your perfect day in the village.
90 min · Tarrytown & Sleepy Hollow
14:55
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
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: Su–Th 10:30AM–10:45PM, F Sa 10:30AM–11:45PM
Overnight here
e.g. Castle Hotel and Spa · Courtyard Tarrytown Westchester County
Day 2 Beacon
- Transit
- 1h19
- Finish
- ~12:00
- Temperature
- 6.2°C–16.9°C
- Rainy days
- ~18
- Daylight
- 10.9h
10:10
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: F–M 10AM–4PM; April–October: Th-M 11AM–6PM; November–December: Th-M 11AM–4PM
11:10
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: W–F Su 1–5PM, last tour at 4PM
Day 3 Rhinebeck
- Transit
- 1h32
- Finish
- ~15:45
- Temperature
- 5.1°C–16.1°C
- Rainy days
- ~18
- Daylight
- 10.8h
10:00
Rhinebeck Post Office tools.usps.com
Admire WPA-era murals and historic architecture.
50 min · Rhinebeck
open: M-F: 9:00AM-5:00PM, Sa: 9:00AM-3:00PM, Su: closed
11:05
Old Rhinebeck Aerodrome oldrhinebeck.org
Witness airworthy vintage aircraft taking flight.
50 min · Rhinebeck
12:10
Wilderstein wilderstein.org
Explore a stunning mansion in beautiful park-like grounds.
50 min · Rhinebeck
13:15
14:45
Bread Alone breadalone.com
Relish sweet and savory pastries with excellent coffee.
60 min · Rhinebeck
open: Daily 7AM-5PM
🔍 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.