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Discover the Charm of Massachusetts: My Must-Visit Favorite Spots
24
items A local’s guide to leaf peeping, shoreline strolling, hiking trails, good eats, and charming shops
through my eyes.
Sections
5
Massachusetts Fall Foliage Guide: Best Places to See Stunning Autumn Color
🍁 Why Fall in Stockbridge Is So Special
🍁What to Wear Leaf Peeping in Massachusetts: Cozy Looks for Crisp Fall Adventures🍂 There’s nothing quite like autumn in Massachusetts — the air turns crisp, cider flows freely, and the trees put on a show that rivals any runway. Whether you’re str...
Visit Shelburne MA
Old Cape Cod
Massachusetts Fall Foliage Guide: Best Places to See Stunning Autumn Color
Calling all leaf peepers! There’s nothing quite like autumn in Massachusetts—when the crisp air rolls in and the landscape transforms into a breathtaking canvas of gold, crimson, and amber. In this guide, I’m sharing my favorite spots to soak in the ...
Mount Greylock: A Leaf Peeper’s Dream in the Berkshires
Rising 3,491 feet above sea level, Mount Greylock is the highest point in Massachusetts—and an absolute must for fall foliage lovers. As autumn takes hold, the mountain becomes a sweeping tapest...
Mount Greylock State Reservation
Kennedy Park is leaf-peeping at its finest: expansive forest panoramas, accessible trails, peaceful overlooks, and a rich tapestry of fall hues. Whether you’re hiking, biking, or just soaking it all in, it’s a must-visit spot to truly embrace the Ber...
Kennedy Park (2025) - All You Need to Know BEFORE You Go (with Reviews)
🍁 Why Fall in Stockbridge Is So Special
Timeless small-town beauty: The town seems lifted from a Norman Rockwell painting, with colonial storefronts, crisp autumn leaves, and the iconic Red Lion Inn anchoring downtown. Walking Main Street in October feels like stepping into a vintage postc...
Fall in Stockbridge is a picture-perfect mix of nature, history, and art, wrapped in cozy village character. From glowing forests to charming boutiques, peaceful hikes to festive gardens, it’s an unforgettable autumn escape tucked into the heart of t...
Visit
Norman Rockwell Museum: Spend an afternoon exploring nearly 1,000 original Rockwell works and the archives of American illustration. A must-see for art lovers and a perfect complement to fall foliage viewing.
Visit
Berkshire Botanical Garden: This beautiful 24‑acre garden bursts with seasonal color. Their annual Harvest Festival each Columbus Day weekend brings artisan vendors, food trucks, live music, hayrides, and hot cider amid autumn blooms
Berkshire Botanical |
Wander flat, scenic paths over the Housatonic River—or tackle the more rugged Ice Glen trail into a moss‑covered ravine. For sweeping views, Laura’s Tower trail delivers a rewarding climb. 
Goodrich Park - Laurel Hill Association
Just a short drive, you’ll find Windy Hill Farm offering apple picking and cider donuts surrounded by autumn leaves. Enjoy café treats like European pastries or cozy local dining once you return to town.
Windy Hill Farm, Inc.
After a long day of leaf peeping, treat yourself to a cozy, satisfying meal at Once Upon a Table—a charming spot tucked away in the heart of town. Here, you’ll enjoy thoughtfully prepared dishes made with peak-season ingredients sourced from local fa...
ABOUT | Once Upon a Table
A picture-perfect backdrop of vibrant fall foliage in the rolling hills—crimson, gold, and amber trees accent the traditional red barns and fields. The farm market offers farm-fresh cider, donuts, homemade maple treats, vegetables and locally raised ...
Ioka Valley Farm
🍁What to Wear Leaf Peeping in Massachusetts: Cozy Looks for Crisp Fall Adventures🍂 There’s nothing quite like autumn in Massachusetts — the air turns crisp, cider flows freely, and the trees put on a show that rivals any runway. Whether you’re str...
New England fall means layering and nothing beats a good base layer like a soft tank top.
Women's Bean's Layering Tank
Layering essentials for cool fall days.
Women's Mountain Classic Fleece Vest
I’ve said it before and I’ll say it again—layering is everything during New England fall. This moisture-wicking long sleeve is the perfect base for a day spent hiking the trails. Lightweight, breathable, and built for whatever the weather throws your...
Swiftly Tech Long-Sleeve Shirt 2.0 *Waist Length | Women's Long Sleeve Shirts | lululemon
• Mid‑layer for hiking or cooler evenings: Perfect for spring, fall, and mild winter layering.
• Active layer path: Breathable grid fleece is ideal under a wind or rain shell when you’re on the move.
• Travel or casual wear: Great for layering on p...
Women's Essential Hike™ Grid Fleece Full Zip Jacket
Whether you’re a seasoned hiker or just getting into outdoor adventures, Merrell hiking shoes are a solid, trusted choice for reliable trail footwear.
Comfort: 5/5
Merrell is known for its out-of-the-box comfort. The shoes feature excellent arch su...
Merrell Men's Moab 3 Waterproof Hiking Shoe
Style, comfort, and practicality. Here’s why they’re my go-to: Flattering and functional, the high waist gives great coverage and pairs perfectly with cropped or tucked-in tops for a streamlined look. Unlike bulky cargos, these have a more tailored,...
High-Waisted SleekTech Wide-Leg Cargo Pants | Old Navy
Water-resistant and wind-fighting, making it ideal for unpredictable fall weather. Oversized fit allows for a hoodie or fleece underneath without feeling bulky. It looks just as cute layered over leggings and boots at a cider mill as it does on an ac...
SleekTech Oversized Cinched-Waist Jacket | Old Navy
Visit Shelburne MA
Apex Orchards is much more than a pick‑your‑own farm—it’s a peaceful western Massachusetts retreat perfectly suited for leaf‑peeping, fruit harvesting, and autumn memories. Whether you’re strolling scenic fields, sampling local goodies, or watching t...
Apex Orchards
A former trolley bridge turned lush garden walkway over the Deerfield River.
The Bridge of Flowers
Formed by glacial meltwater, these swirling rock formations are smooth, circular holes in the granite riverbed—some as deep as 39 feet. Best viewed from the pedestrian bridge or near the Salmon Falls.
Glacial Potholes (2025) - All You Need to Know BEFORE You Go (with Reviews)
Take a ride on a restored trolley car or explore a kid-friendly museum filled with transportation history.
Ride the Trolley - Shelburne Falls Trolley Museum
Casual dining with scratch made items.
Baked Restaurant Shelburne Falls
Great coffee, beer, live music, and cozy vibes.
Mocha Maya's
A lovely gallery-style shop featuring local artists and crafts.
Shelburne Artisans' Cooperative (2025) - All You Need to Know BEFORE You Go (with Reviews)
Old Cape Cod
• For Nature Lovers: A breathtaking array of themed gardens and horticultural treasures throughout the year.
• For Families: Interactive spaces like Hidden Hollow, adventure elements, and carousel nostalgia.
• For History Buffs & Art Aficionado...
Heritage Museums & Gardens