I can’t believe we’re already in November! I’ve been loving the cool, crisp weather lately — those sunny fall days that make everything feel golden.
With this amazing weather, I thought it would be fun to share a fall day itinerary for Westchester County. If I were spending a perfect autumn day here, here’s exactly how I’d do it:
🍂 Morning: Start With a Festive Fall Hike
There are so many incredible hiking options in Westchester that it’s almost overwhelming.
Turkey Mountain Nature Preserve (Yorktown Heights) — a moderate, two-mile round trip with a steady climb to the summit. On a clear day, you can spot the NYC skyline, Hudson River, and Croton Reservoir.
Kitchawan Preserve (Ossining) — offers a mix of open fields and forest trails, peaceful and easy for all levels.
Ward Pound Ridge Reservation (Cross River) — Westchester’s largest park with over 35 miles of trails for leaf-peeping and wandering.
🍎 Midday: Cider, Donuts & Hudson Valley Flavor
Apple-picking season may be winding down, but the fall fun continues at Thompson’s Cider Mill in Ossining (weekends 10 a.m.–5 p.m.). It’s right next to Kitchawan Preserve, so hike first, then stop in for award-winning cider, cider donuts, muffins, and Hudson Valley honey.
They also sell maple syrup from White Oak Farm, the only commercial producer of pure maple syrup in Westchester County.
Still craving orchard vibes? Visit:
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🍏 Harvest Moon Orchard (RewardStyle Link Placeholder)
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🍎 Outhouse Orchard (Amazon Travel Essentials Link Placeholder)
🕵️♀️ Afternoon: Hunt for Treasures at an Estate Sale
Estate sales are one of my favorite weekend adventures. Companies like Knack of All Trades or Consign It often host them, but sometimes the best ones are those surprise roadside finds.
There’s something magical about exploring a beautiful home and discovering vintage glassware, antique furniture, or even a designer bag at a steal.
🛍️ Late Afternoon: Shop & Lunch in Katonah or Bedford
If I’m in Katonah, I always start at LMNOP for a matcha or coffee and one of their pastries. Then I browse my favorite shops:
Our North, Indigo and HIM by Catherine H., Nine by Ash, Bijou of Katonah, Michael’s Luxury Consignment, Katonah Pasta, Gather, Rubysue, &James, Bedford House, and Majestic Hudson.
Next, I pop over to Historic Bedford:
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MAST – for a cozy lunch (soup, sandwich, or salad)
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Dutchess – skincare & haircare boutique
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Rivay – classic menswear
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La Maison Fête – home-goods heaven
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Bedford Books – local charm
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OHHO The Old Firehouse – chic café serving wood-fired pizza and afternoon drinks on their pea-gravel patio
🛍️ Shopping Essentials: Cozy Fall Sweater | Stylish Tote Bag | Portable Charger
🌙 Evening: Cozy Dinner & Golden Hour Glow
Wrap up your perfect fall day with dinner at one of these local favorites:
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TRUCK (Bedford) — farm-to-table Mexican with organic margaritas
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Bedford Post Tavern — cozy American fare in a rustic-chic setting
Either choice delivers delicious food and that warm, relaxed vibe that makes fall in Westchester unforgettable.
🍁 StacyKnows Tip
Bring a reusable tote for all your goodies — from cider and maple syrup to estate-sale finds and Katonah treasures. You’ll thank me later!
💬 What’s your favorite fall spot in Westchester?
Tell me in the comments or tag me on Instagram @StacyKnows!
