Fall Daytrips - Leaf Peeping

We love the Berkshires in the Fall. Whether you are staying with us this fall or not, we recommend these day trips around the Berkshires so you can enjoy the changing of color and come across some places in the area that are not the first things you see when you Google search. Enjoy with your posse! (But of course, Come Stay!!)

Fall Day Trip #1
Fall Day Trip #2
Fall Day Trip #3
Fall Day Trip #4

Fall Day Trip #1

🍁🚗 As we kick off our new series of classic Berkshire day trips, we’re starting right from our front door in Lee. Buckle up for this lovely autumn drive heading west into the historic towns and rolling hills toward the NY border.

Drop these exact stops into your Google Maps and you're ready to roll:

Starving Artist or Lee's Corner Kitchen, Lee, MA
Stockbridge Coffee and Tea, Stockbridge, MA
First Congregational Church, Great Barrington, MA
Hillsdale General Store, Hillsdale, NY
Olde 1811 Antique Shoppe, Chatham, NY
Balderdash Cellars, Richmond, MA
Berkshire House Stay, Lee, MA

Lee ☕ Meet in Lee: Every great road trip needs a starting line, and beautiful Lee is the place to be. Meet up with your crew for a relaxed morning bite—whether that’s a sweet pastry at Starving Artist or a classic, hearty breakfast at Lee's Corner Kitchen—before we hit the scenic back roads.

Stop 1: Stockbridge Stroll & Shop
🍂 Historic Stockbridge: Park at Stockbridge Coffee & Tea to kick off your stop! Browse gifts at Side Tracks, walk over to the iconic Red Lion Inn to check out Shop Around the Corner, and stroll back up Main Street to pop into Whispered in the Heart, BerkCHEERS, and NeJaime’s—then loop back for a treat at the coffee shop.
✨ Not a shopper? Stroll west down Main Street to take in the historic homes, or walk over to Naumkeag to explore the stunning autumn gardens if you've got the energy!

Stop 2: Great Barrington
🚗 The Drive: Cruising south on Route 7 toward Great Barrington, keep your eyes peeled as Monument Mountain rises up right alongside the road, framed by incredible bursts of autumn color.
🍎 Harvest Stops & Great Barrington Stroll: Right on Route 7 as you head out of Stockbridge, make a quick stop at Windy Hill Farm to pick your own autumn apples or select a pumpkin for the season.
When you get to Great Barrington, park near the First Congregational Church and head out on foot! Browse the unique finds at Fripperie and explore the charming local shops lining Main Street. Afterward, take a peaceful meander along the Riverfront Trail to watch the fall foliage drape over the Housatonic River.
🍔 Lunch Stop: Hop back in the car for a quick drive to Bistro Box (open through October!) to grab a fantastic outdoor lunch in the crisp autumn air before heading further west.

Stop 3: Hillsdale, NY
🚗 The Drive: The journey over to Hillsdale treats you to sweeping, open-air views of the valley as you wind through the Taconic Range and get closer to the New York border.
🛍️ Crossing into New York: Park in front of the Hillsdale General Store and spend a happy hour exploring—don’t forget to check out the antiques upstairs! Step right across the street to HG Kitchen for wonderful cookware and gadgets, and visit Books and Cake on the other side for a wonderfully curated read (and, of course, a sweet slice of cake).
🍎 Cider Stop: If you have time before heading out, make a quick detour over to Little Apple Cidery for a lovely afternoon tasting.

Stop 4: Chatham, NY
🚗 The Drive: Winding your way north from Hillsdale toward Chatham on classic two-lane roads, you glide right through the scenic Harlem Valley and its historic farm hamlets, surrounded by rolling hills draped in vibrant fall foliage.
👻 Historic Wandering in Chatham: Begin your Chatham stop at the Olde 1811 Antique Shoppe—housed in Chatham’s oldest building, it’s an absolute blast to explore (and especially atmospheric around Halloween!). Afterward, wander down Main Street to check out the unique local boutiques and treat your crew to something sweet at Fork and Whisk Bakery.

Stop 5: Balderdash Cellars
🚗 The Drive: Winding your way east from Chatham over toward Balderdash Cellars in Richmond takes you across some of the prettiest country roads in the region—drifting past quiet rural farmlands, over gentle ridges, and down into the peaceful valleys just west of the Berkshires' interior.
🍷 Final stop in Richmond: Make your way over to Balderdash Cellars in Richmond—one of our absolute favorites! Drop in to enjoy some fantastic wine, live music and food trucks on most weekends, and the warmest hospitality from owners Donna, Christian, and their wonderful staff. It’s the ultimate spot to unwind together in the afternoon.

Final Stop: Berkshire House Stay
🏠 Your Home Base in the Berkshires: Why rush home when you can make a full weekend out of it?
Located right in the center of Lee, Berkshire House Stay is the ultimate cozy headquarters for your group getaway. Click for AVAILABILITY.

Fall Day Trip #2

🍁🚗 For our second Berkshire day trip, we are going to do a lovely autumn drive heading north and east and circling back through our historic Berkshire towns, hitting art sanctuaries, flower bridges, farms and gorgeous mountain passes!

Drop these exact stops into your Google Maps and you're ready to roll:

Patisserie in Lenox MA
Three Sisters Sanctuary in Goshen, MA
Bridge of Flowers in Shelburne, MA
Hicks Family Farm in Charlemont, MA
Hairpin Turn Overlook or Golden Eagle Restaurant on Mohawk Trail, MA
Second Drop Coffee House, Lanesborough, MA and/or Mt Greylock Visitor's Center
Berkshire House Stay, Lee, MA

Start with ☕morning sweetness in Lenox: Start your journey with a quick stop in charming Lenox. Pop into Patisserie for incredibly friendly service, French pastries and fresh coffee. Fuel up before heading out on the back roads.

Stop 1: Three Sisters Sanctuary and maybe a stop at Devries Sculpture Garden
🚗 The Drive: From Lenox, you can cruise east toward the hilltowns. The roads wind through quiet woodlands and rolling countryside as you make your way into Goshen. If you want to make a pitstop before Goshen, put DeVries Sculpture Trail in your navigation. Gorgeous sculptures and beautiful poetry on this lovely free outdoor exhibit.
✨ Whimsical Art & Gardens: Once you make it to Three Sisters, you can step into a magical sanctuary. Wander through perennial gardens, sparkling glass mosaics, and standing stones. Make sure to find the giant mosaic dragon. Three Sisters is an inspiring, creative oasis unlike anywhere else.

Stop 2: Bridge of Flowers, Shelburne, MA
🚗 The Drive: Continuing north and east along Rt 112, you'll glide along scenic roadway. You may want to make a stop to take a picture at Ashfield Lake or Atherton Farms right off RT 112 before hitting the historic village of Shelburne Falls.
🌸 A Floral Masterpiece: Take a leisurely walk across the historic Bridge of Flowers, a former trolley bridge now transformed into a breathtaking explosion of late-season autumn blooms, cascading vines, and stunning river views. If you are ready for a coffee break, hang out for a bit at Red Dalia Coffee for refreshment of ice cream. (Northeast end of the bridge.)

Stop 3: Hicks Family Farm, Charlemont, MA
🚗 The Drive: Head west onto the famous Mohawk Trail (Route 2), about 15 minutes into the mountains toward Charlemont and make this Autumn stop.
🎃 Hicks Family Farm: Visit the farm animals, wander through the corn maze, grab fresh seasonal goodies, pick out your autumn pumpkins, and enjoy the true rustic rhythm of a 5th-generation family farm.

Stop 4: Hairpin Overlook and the Mohawk Trail, NY
🚗 The Drive & The View: Continue west and climb higher along the legendary Mohawk Trail as the road hugs the mountainside.
⛰️ Epic Overlooks: Pull over at the famous Hairpin Turn Overlook or stop by the Golden Eagle Restaurant area to take in the panoramic views looking over the Hoosac Range blanketed in vibrant fall foliage.

Stop 5: Mount Greylock and/or the Second Drop Farm and Coffee House
🚗 The Drive: Looping south through the scenic hills, your return route brings you down toward the northern valley past Mount Greylock. You can hit the Mt Mount Greylock State Reservation Visitor Center for a fantastic view before a break at:
☕ Afternoon Pick-Me-Up: Second Drop Farm and Coffee House in Lanesborough. Grab some fall produce and rest with a cup of coffee and light snack from this family operated farm and shop.

Final STOP: Berkshire House Stay
🏠 Your Home Base in the Berkshires: Why rush home when you can make a full weekend out of it?
Located right in the center of Lee, Berkshire House Stay is the ultimate cozy headquarters for your group getaway.

With plenty of space featuring 5 bedrooms and 5 baths, a fantastic private backyard, and a wonderful porch for morning coffee or evening unwinding, there is plenty of room for everyone to spread out and relax together.

✨ Ready to gather your crew? Share this page with your travel partners, plan your autumn escape, and come stay with us! Skip the platform fees and save 15% mid-week for Fall using code WEEKDAY15. Click for AVAILABILITY.

Fall Day Trip #3

🍁🚗 For our third Berkshire day trip, we are going to do a lovely autumn drive heading east and south circling back through our historic Berkshire towns, hitting wildlife sanctuary, beautiful lake, farmstands with mazes and gorgeous mountain views!

All these adventures are on the 2 lane roads with mountains and forests all around. We have added quite a few pit stops for photo ops, but there are a dozen more places to stop. We just want to get you back before dark! (spooky Halloween time in the Berkshires!)

Drop these exact stops into your Google Maps and you're ready to roll:

Lee's Corner Kitchen in Lee MA
Frances Rice Wildlife Refuge, MA
Carm's Restaurant in Chester, MA
Lake Garfield Beach in Monterey, MA
Taft Farms in Great Barrington, MA
Evangeline Coffee and Books in Housatonic, MA
Berkshire House Stay, Lee, MA

Starting Point: Lee's Corner Kitchen (Lee) 🥞 Make your plans for the day over breakfast at Lee's Corner Kitchen. The owners are lovely and you can pretty much get your breakfast made to order. Fuel up before the adventure.

Stop 1: Frances Rice Wildlife Refuge (MA) and maybe Glendale Falls

🍂🚗The Drive: From Lee, you will cruise east. Then head up Route 8 through the town of Becket. If you want to stop in Becket, they always have fun things at the Becket Art Center or coffee at Neon Newt or if the Antique place next door is open, I always find a treasure. Then continue north on Rt 8 to Rt 143 East and maybe a photo stop at Ashmere Lake Boat Ramp. You will then hit Peru, MA and head south to the Frances Rice Wildlife Refuge.

🌲Woods & Wildlife: Once you make it to the Frances Rice Sanctuary, take some time for some lovely strolling and photo ops among the wooded trails.

Stop 2: Carm's Restaurant (Chester, MA)

🍁🚗 The Drive: Getting back on Rt 143 heading east and south, enjoys the views. If you want another stop, we love Devries Sculpture Garden and Gallery. Lovely outdoor sculptures complete with beautiful poetry throughout the trail. You can also make a stop at Glendale Falls for a little hike or just a photo opp.

🚂 Rail History: Chester is a historic hilltown famous for rugged mountain rail history. Before lunch at Carm's, stop at the Chester Railway Station Museum. Housed in a restored 1840s train station, see the rich railroad history, walk along the old tracks, and imagine the days of the steam engines. If you are ready to eat, enjoy lunch at historic (100+ years)Carm's. Enjoy a burger or hearty sandwich outside at their picnic tables. If you want to do a little side drive, add Sunny Mountain Farm as a pitstop - Huntington MA 10 miles out of way, to pick up a pumpkin, some bread or peruse the crafts in the market!

Stop 3: Lake Garfield Beach (Monterey, MA)

🍂🚗 The Drive: We have to get back on track, so much more to see! Head west Rt 20 ( with a drive through the Sherwood Forest) and then south on Rt 8 down to Otis and then head West on Rt 23. You will pass the lovely Otis Ridge Ski Center, then West Otis to the sweet town of Monterey, where you will take a pitstop and Garfield Lake Beach.

🎃 Monterey and Garfield Lake: Sometimes there is activity at the Monterey Community Center, could be an art show or music. Teeny Tiny downtown. And if you want a couple pitstops here, try the Bidwell House and Museum or Grenadier Pottery which offers an opportunity to visit a working studio and view pottery with a gallery setting.

Stop 4: Taft Farms, (Great Barrington, MA)

🍁🚗 The Drive & The View: You will get back on Rt 23 heading west. Here are a few places you may want to stop on the way to Taft Farms. Roadside Café for a Malt, and then next door to Gallerie 271 for some culture. Rt 23 merges to Rt 183 over to Great Barrington, where of course you can stop, but we have lots still to do. You will go north on Rt 7 where you may want to make an antique pitstop at And All That Jazz before the stop at Taft Farms.

🎃 Taft Farm: Farm life here. Pick your pumpkin, plus you can get gourds, squash and all the good vegetables. You can also do a farm walk and enjoy the corn maze. Check out the store and enjoy snack out on the picnic tables.

Stop 5: Evangeline Coffee and Books (Housatonic, MA)

🍂🚗The Drive: You can take a side route and make a quick stop at the Guthrie Center to see and then head to Housatonic.

☕ Afternoon Pick-Me-Up: Evangeline Coffee and Books in Housatonic may be open by the time you read this (It is BRAND NEW - I am super excited to check it out! Have a coffee and check out what Sara has put together for your reading pleasure. If you are looking for some fresh baked goods to take home, stop at Berkshire Mountain Bakery, get some bread and cookies for the evening and then you will discover the love and start having the yumm shipped to your home!!

Final STOP: Berkshire House Stay

🏠 Your Home Base in the Berkshires: Why rush home when you can make a full weekend out of it?
Located right in the center of Lee, Berkshire House Stay is the ultimate cozy headquarters for your group getaway.

Fall Day Trip #4

🍁🚗 For our fourth and final Berkshire day trip, we’re pairing breathtaking autumn views along the road with a brainy, cozy destinations: the creak of old wooden floors, aged paper, and charming independent bookstores. Ready to dive in?

Drop these exact stops into your Google Maps and you're ready to roll:

🥐 Lost Lamb, Stockbridge
🎨 137 Front Street, Housatonic, Great Barrington
📚 Yellow House Books, Great Barrington
🍰 Books and Cake, Hillsdale NY
📖 Shaker Mill Books, West Stockbridge
🏛️ The Mount, Lenox
🍷 Bookstore and Get Lit Winebar, Lenox

Let's meet at the Lost Lamb Patisserie in Stockbridge. You can enjoy a stroll around the town, wander into the Red Lion Inn and the group can get a pastry and fill up their coffee mugs over at Lost Lamb Patisserie.

🚗 En Route to Stop 1: Housatonic As you wind your way west and south (RT102 and RT 183) you’ll glide through the Stockbridge Country Club, down tranquil riverbanks, flanked by autumn ridges and quiet country lanes leading toward the creative heart of the valley.

Stop 1: Evangeline Coffee and Books (Housatonic) Keep your eye out, Evangeline may not quite be open. (this is still the best drive for the next stop). If they are not open yet, make a quick stop at Pleasant and Main for some unique antiques. If they are open, Books and Coffee, or Coffee and Books, and some stationary! A neighborhood coffeeshop and bookstore based in Housatonic. Making the everyday extraordinary. They also have a lovely selection of stationary and pens. Start that journal!

🚗 En Route to Stop 2: Housatonic to Great Barrington As you follow the curves of the Housatonic River south (Rt 183), you’ll cruise past Monument Mountain on the left and farm fields on the right. You can do a bakery stop at Berkshire Mountain Bakery and then check out Taft Farms before hitting downtown Great Barrington.

Stop 2: Yellow House Books (Great Barrington) This place has lots of history for Berkshire book lovers. Anything you want related to the Berkshires is going to be here. In addition, it is a haven for used and rare finds (complete with a resident cat!). Hang at the Yellow House, then next door for a little consignment therapy. And of course all of Great Barrington's Main Street for kitchen (one Mercantile), clothes (Main Street), cheese(Rubiner's Cheesemongers), coffee (Café Holli) and treats (Coco's Candy).

🚗 En Route to Stop 3: Great Barrington over the New York Border to Hillsdale Head south out of Great Barrington and then west over the state line on Route 23, winding up and over the crest of the Taconic Mountains where valley views of fall foliage stretch out below. You will pass Catamount Resort. If you are feeling adventurous, and they are open, do the zip line tour and go over the canopy of foliage!

Stop 3 Books & Cake (Hillsdale, NY) This is a library in a friend's house, where you can have cake(and eat it too) and coffee and peruse. They have organized the books by "Read if you need…", so chat with the team and get a recommendation. This is a sweet little corner right in the center of Hillsdale. If you want to stick around, wander into Hillsdale General Store, and across the street at HGS Home Chef, and then have a bite at the Hillsdale House.

🚗 En Route to Stop 4: Hillsdale back into Massachusetts to West Stockbridge - Winding back east through the rolling hills, drive north on RT 22 on the picturesque country roads blanketed in fallen golden leaves. You will head west on RT 102 to drop you into West Stockbridge.

Stop 4 Shaker Mill Books (West Stockbridge) - Shaker Mill is housed in a 19th-century mill building, this shop features over 30,000 rare and used titles. Where history literally lives on the shelves. Lots of local art to enjoy and very knowledgeable team. Look for the book sculptures! And don't miss the views of the river from the back deck. Absolutely take a wander through the tiny town of West Stockbridge. If the Foundry is open, stop in, walk across the river and enjoy a couple antique stores, galleries and a market to fill up. If you need a caffeine fix, stop at No. Six Depot.

🚗 En Route to Stop 5 & 6: West Stockbridge to Lenox - This short scenic drive brings you past the historic edges of Tanglewood, where towering maples and oaks form a brilliant, fiery overhead canopy tunnel leading right into sweet Lenox. You may want to make a pitstop at Olivia's Overlook (just 2 miles from West Stockbridge on route to Lenox) for some great vista shots.

Stop 5 The Mount Bookstore (Edith Wharton's Home - Lenox) Make sure you schedule plenty of time here. After picking your books, stroll the grounds and find a bench to rest and read. You’re buying books in the house where The House of Mirth was lived. Their bookstore is small but impeccably curated with a focus on women writers and Wharton herself.

Stop 6 The Bookstore & Get Lit Wine Bar (Lenox) This is where you go for a "grown-up" afternoon. Sophistication meets soulful. Ask Matt (the owner) for a recommendation, over a glass of wine. He’s been the soul of this place for 40+ years. You can noodle around the shelves for hours. It’s more than a shop; it’s a literary sanctuary where the conversation is as good as the collection.

After a full day of chasing autumn colors, discovering rare first editions, and sipping wine among the stacks, head back to Berkshire House Stay to unpack your literary treasures. Pour a warm mug or uncork a bottle, sink in and lose yourself in a brand-new story as the autumn wind rustles outside. Your ultimate Berkshire fall getaway awaits—book your stay today and let the adventures begin! 🏡✨