A Getaway to the Okemo Valley Region of Vermont

After living in New England for 6+ years, I finally took a trip up to Vermont and checked off my final New England state. I spent a couple days in the Okemo Valley region, a beautiful area in South Central Vermont where creativity, arts, and culture meet small-town charm. From artisan cheese and local wine to gallery strolls, live theater, and handcrafted local products, it’s the perfect spot for a getaway if you’re looking to immerse yourself in arts and culture.

Officially kicking off July 1, the Arts & Culture Village Strolls is your chance to explore it all at your own pace across 12 picturesque towns. With a self-guided map that you can find at Your Place in Vermont, you can wander from village to village discovering unique spots, some well-known, and some off the beaten path. It’s the perfect blend of adventure, relaxation and culture.

Here’s how I spent a perfect 48 hours in the Okemo Valley!

Day 1 - Arrival in the Okemo Valley

Scenic Drive from Connecticut

Driving from Connecticut to Vermont is one of the things that makes me appreciate New England so much. It’s such an easy, scenic trip, and in just a few hours, you can be somewhere completely different and beautiful. I made a couple of pit stops along the way including breakfast and coffee at Heirloom Market in Old Wethersfield, then a quick visit to the Vermont Country Deli in Brattleboro, which I highly recommend (get the mac and cheese!). All in all, it took about three hours from Fairfield County to southern Vermont, making it an ideal and super doable weekend getaway.

Check-in at The Castle Hill Resort and Spa
📍 171 Castle Hill Dr, Proctorsville, VT 05153
Once we arrived to the Okemo Valley, we checked in at the Castle Hill Resort & Spa in Proctorsville, Vermont, a historic and elegant property tucked into the Green Mountains. Built in 1905 for Governor Allen Fletcher, the mansion still features original details like hand-carved woodwork, Tiffany lighting, and was even the first home in Vermont with electricity. You can choose between beautifully restored rooms in the castle or modern condos nearby. The on-site Aveda spa, fine dining, and close proximity to Okemo Mountain make it a great spot for both relaxation and outdoor adventure, whether you're planning a romantic weekend or a family vacation.

Dinner at Murdock’s on the Green

📍 42 Village Green, Proctorsville, VT
After settling in at the Castle Hill Resort, I drove over to Murdock’s on the Green, a casual restaurant steps away from the Proctorsville Town Green. The restaurant has hearty, farm-to-table comfort food like burgers, steak tips, and mac and cheese, all made with fresh ingredients from local farms and vendors. I ordered the scallop special and a blueberry lemonade cocktail, which were both great. I enjoyed sitting outside on the patio overlooking the green on a beautiful summer day. After dinner, it was time to head back to the resort and rest up for a busy day ahead.

Day 2 - Arts & Culture Village Stroll

Morning: Exploring Ludlow
Singletons General Store
📍 356 Main Street, Proctorsville, VT
Before a packed day in the Okemo Valley, it was time to start the day off with breakfast at the local general store. After doing some research, I picked Singleton’s General Store, and I am so glad I did. It’s a Vermont staple that is part grocery, part deli, part sporting goods shop, and all heart. They’re famous for their smoked meats, and their deli sandwiches are a must-try. Beyond food, you’ll find everything from Vermont craft beer and maple syrup to hunting gear and quirky gifts. It’s the kind of place where the staff remembers your name and the aisles are packed with character. I opted for a breakfast sandwich with eggs, smoked sausage, maple butter, cheddar cheese and a hash brown. It was incredible!

Create Together @ Fletcher Farm
📍 611 VT-103, Ludlow, VT
After breakfast, it was time for day of exploring the Okemo Valley. I started my day at Create Together at Fletcher Farm, a welcoming art space in Vermont that offers workshops, classes, and studio access for all skill levels. From quilting and painting to weaving, sewing, and soon pottery and metalwork, they provide hands-on opportunities to learn and create in a supportive environment. You can take short sessions or multi-week courses, rent studio time to work independently, or become a member for added benefits. They also offer scholarships, payment plans, and discounts for local residents, making creativity accessible to everyone.

The Depot Street Gallery
📍 44 S Depot St, Ludlow, VT
After visiting Create Together, we headed over to the Downtown area of Ludlow and stopped into Depot Street Gallery, a hidden gem that brings together the work of over 150 local artisans. It’s the kind of place where you can easily lose track of time, browsing everything from handmade gifts to one-of-a-kind pieces for your home. It’s also home to The Silver Spoon, where artist Steven Manning turns antique silverware into beautiful, functional jewelry and art. I found so many great local items and could have bought everything in the store! After Depot Street Gallery, you can walk around the corner and visit the local bookshop - the Book Nook.

Lunch & Ice Cream Before the Theater

The Hub in Weston
📍 705 Main Street, Weston, VT

My next stop was a show at the local Weston Theater, but before that, it was time to have some lunch in Weston. The Hub in downtown Weston is a cozy, farmhouse-style café that really captures the Vermont vibe. Open for lunch Wednesday through Sunday, it’s a great spot to grab a bite before or after catching a show at the Weston Theater. The café is set in an old farmhouse with just 27 seats, serving up fresh, seasonal dishes like soups, tasty sandwiches, and creative salads, all made with local ingredients. I ordered the classic grilled cheese (when in Rome!) and an iced maple latte - both were excellent!

Green Mountain Sugar House
📍 820 Vermont Rte 100, Ludlow, VT

I needed a little sweet treat after lunch, and you can’t come to Vermont without getting a maple creemee so my next stop was at Green Mountain Sugar House. This family-run spot on Route 100 has been serving up these silky, maple-infused soft serves for decades. Made with pure Vermont maple syrup, they're the perfect balance of sweet and creamy, without being overly sugary. While you’re waiting for your maple creemee, you can sit lakeside or browse the charming gift shop.

Afternoon: Theater in Weston
Almost Heaven: John Denver’s America at Weston Theater
📍 703 Main St, Weston, VT
Now it was time to visit the Weston Theater, a small but impressive award-winning regional theater that’s been around for decades. While I was in town, they were running Almost Heaven: John Denver’s America. I wasn’t totally sure what to expect, but it ended up being such a fun and surprisingly moving tribute to his music. They covered all the classics—“Take Me Home, Country Roads,” “Annie’s Song,” and of course, “Leaving on a Jet Plane.” The whole show had this easy, nostalgic vibe that really captured the warmth and simplicity in Denver’s songs without overdoing it. The actors were so impressive playing several instruments during the show.

Vermont Country Store
📍 703 Main St, Weston, VT
After a show at the Weston Theater, the Vermont Country Store is a must-visit. I love an old fashioned general store and this place fits the bill! Started by Vrest and Mildred Orton, it began as a small catalog business out of their garage and grew into one of Vermont’s most iconic spots. The store is packed with everyday basics and hard-to-find favorites: flannel pajamas, cast iron pans, wooden toys, and personal care products you probably thought were discontinued. You’ll also find shelves of maple syrup, pantry staples, and more nostalgic candy.

Evening: Dinner at Castle Hill Resort
Castle Hill Resort Dining Room
📍 703 Main St, Weston, VT

Located in the castle, the atmosphere is warm and historic, think wood-paneled walls, candlelit tables, and that charming old-world vibe that just makes you want to linger. The food was incredible too, thoughtfully prepared, seasonal dishes that somehow managed to feel both upscale and comforting.

Day 3 - Art, History & Departure

Chester Arts Scene
Fischer Arts
📍 102 The Common, Chester, VT
It was my last morning in Vermont and my first stop was Fischer Arts in Chester, Vermont, a cozy gallery on the village green that celebrates the connection between art and nature. Founded by Iris Fischer-McMorrow, the space features a unique mix of antique botanical prints, maps, and vintage engravings alongside contemporary paintings, ceramics, jewelry, photography, and handmade gifts from New England artists. Each room is thoughtfully arranged around themes like ocean life, forests, and mushrooms. A portion of every sale supports conservation efforts, making it a place where creativity and care for the environment go hand in hand.

Smokeshire Design
📍 3630 VT-103, Chester, VT
After visiting Fischer Arts, I drove a few minutes over to Smokeshire Design which sits just off Route 103 between Ludlow and Chester, in a beautifully restored old general store building that feels both historic and fresh. Inside, you’ll find a carefully curated selection of handmade furniture, pottery, glassware, jewelry, linens, and home goods, all created by Vermont artisans. Highlights include hand-thrown bowls, custom pieces by Hugh Pennell and other local makers, plus their own Bourbon barrel–aged maple syrup for sampling and purchase.

A Presidential Close to the Trip
President Calvin Coolidge Historic Site
📍 3780 VT-100A, Plymouth, VT
For my next and final stop on trip, I drove up to Plymouth to visit the Calvin Coolidge Historic Site, which was one of my favorite stops of the trip. The grounds are absolutely stunning and if you love American history, this is a must see. It’s the childhood home of our 30th president, and the place where he was actually sworn into office in 1923. You can wander through the original family farmhouse, check out the old schoolhouse, visit historic barns, and even see the Plymouth Cheese Factory, still making cheese the old-fashioned way. The whole village is beautifully preserved, giving you a real feel for rural life in the early 1900s and a glimpse into what shaped Coolidge’s simple, down-to-earth approach to leadership.

Plymouth Cheese
📍 106 Messer Hill Rd, Plymouth, VT
After you’re done at the Calvin Coolidge Historic Site, you can wander over to Plymouth Cheese which is classic New England! Tucked inside a historic 1890s creamery built by President Coolidge’s father, they’re still making cheddar the old-school way, with raw milk from a local herd and lots of care. The vibe is simple and unfussy, with a tiny museum upstairs and windows where you can peek at the cheesemaking in action. Their Original Plymouth cheddar is sharp, rich, and just the right kind of crumbly, and the truffle and peppercorn flavors are definitely worth a try.

A Stop in Grafton on the Way Home

Grafton MKT
📍 162 Main Street, Grafton, VT
On the way home to Connecticut, I stopped in Grafton for lunch and fell in love with this quaint little town. For lunch, I stopped at Grafton MKT, an old fashioned general store in the heart of downtown Grafton. It functions as part café, part market, offering a great selection of locally made goods, cheeses, fresh coffee, and simple, satisfying food. Their classic grilled cheese is made with Vermont cheddar, thick sliced white bread, and pressed with herb butted. It was the perfect ending to a fantastic trip!