Antiquing in the Berkshires: A Two-Day Vintage & Antiques Road Trip

Antiquing in the Berkshires is the latest stop in my Antiquing in New England series, where I share a shop, a stay, and a find in vintage-loving towns across the Northeast. In this post, you’ll discover a curated two-day road trip through the southern Berkshires from bargain treasures to high-end showstoppers, starting in North Barrington and ending in charming Sheffield. I’ll take you inside local favorites like Antiques Center and All That Jazz, share my stay at the cozy and historic Wainwright Inn B&B, and highlight my favorite vintage finds along the way. Whether you’re mapping out your next antiquing getaway or just love to travel through vintage stories, this guide offers the shops to visit, the places to stay, and the inspiration to style your own collected home.

Love road-tripping for vintage treasures? This post is part of my Antiquing in New England series, where I share a shop, a stay, and a find in charming towns across the region. Explore more hidden gems and vintage haunts throughout New England.

Antiquing in the Berkshires: First Stop at Antiques and All That Jazz in Great Barrington

If you’re antiquing in the Berkshires and love a good treasure hunt, Antiques and All That Jazz in Great Barrington is a must-visit. I left Manchester, Vermont, around 10:30 a.m. and arrived just before noon, perfect timing for a day full of vintage finds. This spot quickly became my favorite for budget-friendly antiques thanks to its charming vibe, layered vendor booths, and eclectic selection. From antique kitchenware and classic dishware to vintage clothing and one-of-a-kind furnishings, there’s truly something for every style and price point. Room after room opens up with fresh discoveries, and you’ll want to take your time here. Keep scrolling to see what I found and how I styled it!

What I Found While Antiquing in the Berkshires at Antiques and All That Jazz

This stop was packed, room after room, with well-stocked vendor booths, each brimming with character and charm. From high-end statement pieces to budget-friendly treasures, this shop had one of the most diverse and inspiring selections I’ve seen while antiquing in the Berkshires. Get Directions

Here’s what I brought home: a 100% cashmere scarf in my favorite soft blues and browns for just $18, a set of four Johnson Brothers Ironstone Windsor appetizer plates in a rich brown and white transferware pattern for $20, plus a coordinating platter for another $20. I also couldn’t resist a small painted side table in a gorgeous mix of blues and browns, perfectly worn and ready to add a vintage touch to our living room.

And while I couldn’t take everything home, here are a few other standout pieces that caught my eye during my visit:

“Antiquing is the art of finding what you never knew you needed, in the places you never knew you’d love.”

Antiquing in the Berkshires: Touring the High-End Beauty of The Berkshire Galleries of Great Barrington

If you’re antiquing in the Berkshires and craving something extraordinary, stop at The Berkshire Galleries of Great Barrington. This isn’t your average antique shop; this is a fully curated, high-end showcase that feels like walking through an interior designer’s dream. From Turkish rugs and antique quilts to marble busts, primitive trunks, and rare architectural pieces, every booth is thoughtfully styled to perfection. Get Directions

Even if you’re not in the market for investment pieces, this gallery is a destination in itself. It’s a feast for the eyes and a photographer’s paradise, offering endless inspiration for anyone who loves antique style, home decor, or design. Whether you’re building a new home, furnishing a historic one, or simply want to browse the best of the best, this is a must-see shop in the Berkshires.

Though I left empty-handed, this shop filled me with ideas and admiration. It’s an inspiring, museum-like experience for anyone who loves beautifully curated antiques.

A Cozy Lunch Stop at Barrington Brewery & Restaurant: Antiquing in the Berkshires

After a morning of driving and treasure‑hunting, it was time for a well‑earned break. I stopped at Barrington Brewery & Restaurant, a charming New England brewery and eatery right off Route 7. Get Directions

Established in 1995, the place feels authentically local: rustic, inviting, and full of character. From burgers and handcrafted beer to pizza and seasonal sides, it’s the kind of spot that hits the sweet spot when you’re mid‑day and mid‑road‑trip. I may not always crave a burger, but this place definitely won me over, perfect for resetting before heading back into the hunt.

Antiquing in the Berkshires: A Charming Stay at the Wainwright Inn in Great Barrington

After a full day of antiquing in the Berkshires, I checked into the Wainwright Inn, a beautiful historic bed and breakfast just minutes from downtown Great Barrington. I stayed in the Edison Room, located on the first floor, and it was absolutely perfect. With its antique canopy bed, spacious layout, and vintage charm, this room felt like a cozy retreat from the rainy evening outside. The entire inn was spotless, peaceful, and full of character, exactly what I look for in a New England stay. Get Directions

The owners couldn’t have been kinder. When I realized I’d forgotten my power adapter, they generously lent me a modern dual charger that worked perfectly with my laptop and phone, such a thoughtful touch! In the morning, I was treated to a full homemade breakfast: scrambled eggs, bacon, home fries, and a fresh fruit cup, all served at the time I requested the night before. French toast was also an option, and everything was delicious.

I spent some time walking the property and snapping photos; every corner of this inn is worth exploring. There’s just something about staying in a charming, old-fashioned bed-and-breakfast that sparks so much vintage decorating inspiration. From the green and white wallpaper and antique signage to the cozy bedroom details, antique rugs, and nostalgic breakfast place settings, it all felt like stepping into a storybook. Whether you’re antiquing for the weekend or simply soaking up the style, the Wainwright Inn is a place that stays with you long after you leave.

Antiquing in the Berkshires: A Morning Visit to Berkshire Great Finds Antiques Art Center & Frame Shop

The next morning after breakfast, I drove the short distance from the inn to Berkshire Great Finds Antiques Art Center & Frame Shop, a sprawling 7,000‑sq‑ft multi‑dealer antiques and collectibles destination. Located in Sheffield, this spot has an eclectic mix, from furniture and vintage tools to oddities and home decor, but I found the pricing to lean more upscale than what I typically see in Maine or Vermont. Still, it’s a fantastic place to browse, get inspired, and soak up the curiosities of antiquing in the Berkshires. Get Directions

One thing that stood out: this shop felt, in large part, geared toward what I’d describe as a more masculine aesthetic, lots of industrial metal, vintage crates, architectural salvage, and rugged furniture. That said, there are absolutely plenty of treasures for everyone: dishes, vases, artwork, and more tucked into corners. While I didn’t find the perfect piece to bring home this trip, I highly recommend this stop for anyone with a vintage instinct and a love for something distinctive.

How I Styled My Berkshires Antique Finds at Home

After unpacking my treasures from this antiquing in the Berkshires road trip, I couldn’t wait to find a home for them. From the vintage Johnson Brothers dishes and cozy cashmere scarf to the painted side table in soft blues and browns, each piece brings back the charm of Great Barrington.

A Vintage Floral Side Table, Styled Two Ways

This little blue-and-brown floral-painted side table was one of those unexpected finds that quickly became a favorite. Lightweight and charming, it’s easy to move and works beautifully in multiple rooms. Most mornings, I use it in the living room to hold my coffee while I sit in front of the fire. And in our sunroom, I’ve started using it alongside the coffee table, its slightly taller height makes it perfect for setting down a cup of coffee while I sit and blog. It’s a small piece with big personality, and a perfect example of why I love antiquing in the Berkshires: practical, pretty, and full of vintage charm.

Brown Transferware Dishes for a Fall-Inspired Hutch Display

These brown-and-white Johnson Brothers transferware appetizer plates and platter were such a fun find on this antiquing in the Berkshires trip, and I couldn’t wait to style them at home. I nestled them into my pine dining room hutch, surrounded by white vintage ironstone, soup tureens, and simple white dishware. To bring in the seasonal charm, I added orange and white pumpkins and gourds for a soft fall touch. The warm brown tones of the transferware give just the right amount of contrast to all the creamy whites, and a little green “Gone Antiquing” sign finishes the look with a playful nod to the hunt. It’s a simple, collected moment that feels just right for the season.

Styling a Blue and Brown Cashmere Scarf for Cozy Holiday Decor

This soft blue and brown 100% cashmere scarf was one of my favorite unexpected finds while antiquing in the Berkshires, and while I may not wear it every day, I absolutely love using scarves like this in my seasonal decorating. For now, I’ve draped it around one of my holiday mannequins (you can see the full post in Christmas Mannequin Decoration Ideas So Cute, They Stole the Table), and it transitions beautifully from fall into winter with its rich, warm tones.

I also love using scarves to tie around vintage skis, drape over snowshoes on the porch, or even line a bread basket or decorative crate. Whether styled on a mannequin, tucked into a vintage basket, or layered into a holiday porch scene, scarves like this one add an effortless, cozy texture that makes any space feel just a little more collected and charming.

And super cute on Ella, too…

What to Know Before Antiquing in the Berkshires

Planning your own antiquing adventure in the Berkshires? Here are a few tips to help you make the most of your vintage road trip through Great Barrington, Sheffield, and beyond:

Antiquing in the Berkshires, One Find at a Time

From the eclectic vendor rooms of Antiques at All That Jazz to the high-end styling of The Berkshire Galleries and the curated charm of Berkshire Great Finds, this antiquing in the Berkshires road trip offered a little something for every vintage lover. Add in a cozy stay at the Wainwright Inn and a hearty lunch at Barrington Brewery, and you’ve got the perfect New England weekend getaway.

I left with a few special treasures, like that floral-painted side table I now use daily, and a heart full of vintage inspiration. I hope this guide helps you map out your own antique adventure through the Berkshires.

Planning a future trip?
Be sure to check out more stops in my Antiquing in New England series, where every post features a shop, a stay, and a find worth exploring. Looking for more antiquing adventures? Visit some of our favorite vintage and antique shopping guides:

Have a favorite Berkshires antique shop or memory to share? Drop it in the comments, I’d love to hear what you’ve discovered!

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