Sleepy Hollow to Hyde Park: A Hudson Valley Fall Road Trip

Sleepy Hollow, pick-your-own apples, and river hills in full color: here's how to plan a fall road trip through New York's Hudson Valley. Plan this trip on paper: the Fall & Holiday USA Road Trip Planner covers 11 fall and holiday road trips, including this one, with routes, best times, cost tables and checklists. Printable PDF, $7: https://therrellian.gumroad.com/l/fall-roa... We cover the region's history, Sleepy Hollow and its Halloween events, apple orchards, Bear Mountain and Storm King, Hyde Park and the Walkway Over the Hudson, where to eat, typical peak-color timing, how to get there, prices, and a 3-day itinerary. ▶ Also plan: Great Smoky Mountains 3-day guide    • Great Smoky Mountains National Park Travel...   Fall color changes week to week. Check the I LOVE NY Fall Foliage Report before you go: https://www.iloveny.com/things-to-do/fall/... Prices and dates are approximate as of fall 2026 and can change. Check each site before you go. Sources (official sites): Sleepy Hollow history https://www.sleepyhollowny.gov/289/History... · Historic Hudson Valley https://hudsonvalley.org/ · Home of FDR https://www.nps.gov/hofr/planyourvisit/fee... · Vanderbilt Mansion https://www.nps.gov/vama/planyourvisit/fee... · Walkway https://walkway.org/visit/ · Bear Mountain https://parks.ny.gov/visit/state-parks/bea... · Storm King https://stormking.org/visit/ · Masker Orchards https://www.maskers.com/dates-hours-prices/ · Fishkill Farms https://www.fishkillfarms.com/pick-your-own Chapters 0:00 Fall in the Hudson Valley 0:23 Sleepy Hollow & the River Towns 2:00 How Sleepy Hollow Got Its Name 4:01 Orchards & the Hudson Highlands 5:30 Hyde Park & the Walkway 6:41 Where to Eat 7:44 What It Costs 9:01 When to Go 10:05 Getting There 11:15 3-Day Itinerary 12:10 Final Thoughts How things work:    / @howitticks-b1k   · Avoid travel scams:    / @scamalertweekly-e6b   Subscribe to Road Trip USA for a new American destination every episode, and tell us in the comments where we should go next. Photo credits (Wikimedia Commons; cropped/zoomed, text added): Public domain / CC0 photos (65): National Park Service (7) and other public-domain works on Wikimedia Commons. CC BY / CC BY-SA photos (23): • Irina S.B., CC BY 4.0: "Broadway at Old Dutch Chu…" https://commons.wikimedia.org/?curid=17802... · "Beekman Avenue in 2025" https://commons.wikimedia.org/?curid=17898... · "Broadway in Sleepy Hollow…" https://commons.wikimedia.org/?curid=17803... • Ɱ, CC BY-SA 3.0: "IrvingHeadstone" https://commons.wikimedia.org/?curid=33435373 • Shinya Suzuki from New York, U.S.A., CC BY 2.0: "Philipsburg Manor (627454…" https://commons.wikimedia.org/?curid=57450805 · "Waterwheel at Philipsburg…" https://commons.wikimedia.org/?curid=46752541 • Dmadeo, CC BY-SA 4.0: "Van-cortland-manor" https://commons.wikimedia.org/?curid=3140799 • Daniel Case, CC BY-SA 3.0: "Mouth of Pocantico River,…" https://commons.wikimedia.org/?curid=36773623 · "Pumpkins on rack at Wrigh…" https://commons.wikimedia.org/?curid=64927154 · "Scarborough station with…" https://commons.wikimedia.org/?curid=36344516 • Bestbudbrian, CC BY-SA 3.0: "Philipsburg Manor (Sleepy…" https://commons.wikimedia.org/?curid=35434040 • Joe Shlabotnik, CC BY 2.0: "Franklin Roosevelt's Mans…" https://commons.wikimedia.org/?curid=13313... • Paulthelawyer, CC BY-SA 4.0: "Bear Mountain Autumn" https://commons.wikimedia.org/?curid=10308... • Roadgeek Adam, CC BY-SA 2.0: "Perkins Memorial Tower -…" https://commons.wikimedia.org/?curid=16655... · "Perkins Memorial Drive -…" https://commons.wikimedia.org/?curid=16655... • Zeete, CC BY-SA 4.0: "Boscobel, Garrison, NY -…" https://commons.wikimedia.org/?curid=66731373 • Ahodges7, CC BY-SA 3.0: "Storm King Mountain Looki…" https://commons.wikimedia.org/?curid=8758283 • ajay_suresh, CC BY 4.0: "The Culinary Institute of…" https://commons.wikimedia.org/?curid=18844... • Ɱ, CC BY-SA 4.0: "CIA Hyde Park Caterina" https://commons.wikimedia.org/?curid=59598366 • Ron Cogswell, CC BY 2.0: "Roth Hall -- Culinary Ins…" https://commons.wikimedia.org/?curid=54143851 • Jonathunder, CC BY-SA 3.0: "DonutHalves" https://commons.wikimedia.org/?curid=9030487 • Karl Thomas Moore, CC BY-SA 4.0: "Palisades Interstate Park…" https://commons.wikimedia.org/?curid=60329679 • RandyMower, CC BY-SA 4.0: "Sleepy Hollow - Philipsbu…" https://commons.wikimedia.org/?curid=72802037 Licenses: creativecommons.org/licenses/by/2.0 · /by/4.0 · /by-sa/2.0 · /by-sa/3.0 · /by-sa/4.0 Maps: original by Road Trip USA (US Census Bureau state outlines). Narration: AI text-to-speech voice. #HudsonValley #SleepyHollow #RoadTripUSA