Okemo Valley Region, VT: It’s Not All About the Hill

WHY GO: The bulk of visitors come to Okemo Valley to ski.  Okemo is, after all, one of the top ski resorts in the Northeast. But like all other Getaway Maven escapes, this one does not focus on the “One Obvious Thing.”

Ludlow VT Sign, Black River Academy Museum

The Okemo Valley Region is comprised of 14 little villages. Ludlow is the largest, followed by Weston and Chester. There is just one traffic light. And that’s in Ludlow. And there’s not one box store.

You can sign up for a 2-day crash-course in an arts & craft project you’ve always wanted to try out. Or, wander the halls of one of the first co-ed Academies in the country (now a great museum), shop like a fiend, eat like a foodie, and stay glamorous in a “castle” built by a Vermont Governor.

In the Fall, back-to-back buses clog the roadways for foliage viewing. To avoid the crowds, better to come in late Spring.

Okemo Valley Attractions

Okemo Mountain, Ludlow VT


It’s what’s been bringing tourists to this region for eons, and new features like the zip-line keep them coming year-round.

Black River Academy Historical Museum, Ludlow VT

VISIT: Black River Academy Museum and Historical Society, Ludlow

Built-in 1888, Black River Academy drew male and female students from 158 towns, 26 states and even Cuba. One was our 30th President, Calvin Coolidge.

Worn Stairs, Black River Academy, Ludlow VT

A rare co-ed school for its day, Black River saw its last graduating class in 1938, when a new High School was built in town. After a stint as a nursing home and then vacant from 1968-1972, the Richardsonian – Romanesque Style building was preserved and opened as a museum in 1973.

This place is worthy of at least an hour – more so for what has not changed. Here, it’s not the walls that talk, but the stairs, worn and warped where hundreds of feet trudged or skipped up and down (hugging the right-hand side each way).

Calvin Coolidge Antics 

A short video shines a light on student life here, including the many pranks the kids would pull. In one case, a donkey showed up in a second-floor classroom. Who led it up there? When asked, the young Coolidge did not confirm or deny.

Other notable graduates of Black River Academy included Ida May Fuller, who received the very first Social Security Check in 1940, and early vacuum cleaner inventor, Frank Agan.

Paul P. Harris, founder of Rotary Club International, spent a few months here before being expelled, amusingly enough, for extreme pranking.

Local Barber, Black River Academy Museum, Ludlow VT

There are several exhibit halls on three floors. The first, on the main floor, designed and built by Ludlow students, resembles Ludlow Main St. 1900. There’s a blacksmith shop, doctor’s office with pre-nursing home adult cradle, a general store, a country store, and a barber shop. Some old-timers have stopped in to reminisce about getting a haircut in that very chair.

Oil jug, Black River Academy Museum, Ludlow VT

Ludlow was known for its five woolen mills. A voluptuous green blown glass jug, one of the prettiest artifacts in the museum, actually contained oil for the mill machines. Back then, aesthetically pleasing and utilitarian were not mutually exclusive concepts.

Interactive and Innovative School Programs

Vermont Tales, Black River Academy, Ludlow VT

On your way upstairs (look down at those worn steps), you can ring the school bell – a favorite of student groups. Students also take giddy delight in pictures of old t-shirts with the school’s acronym – BRA. The second floor was the Assembly Hall. It’s now a repository for the largest Finnish Exhibit in Vermont.

There are also photos of two devastating Ludlow floods – in 1927 and 2011 – and wonderful in-depth stories of local families written by local 6th graders. Apparently, the very creative Ludlow Elementary School teacher, Heidi Baitz, involves the students in joint history projects – a win win for the town and Historical Society.

One Room School. Black River Academy, Ludlow VT

The top floor now serves as a Country School where teachers lead local students in an immersive “One Day in A One Room Schoolhouse.” Kids learn to write with quill pens, do math problems on slate, have period-appropriate snacks, and play outside.

It’s an innovative way to utilize what could have been just another stuffy museum, turning it into a history class, using all the senses. Open June-1st Sat in Sept, Tues – Sat 12-4, Sept-early Oct, Fri/Sat 12-4, $2 adults, under 12 free.

The Black River Academy Museum is one of 10 quirky-romantic places to propose in Vermont.

Buttermilk Falls, Ludlow VT

GO/COOL OFF: Buttermilk Falls, Okemo Valley VT

At the end of Buttermilk Falls Road you’ll find access to this local favorite swimming hole. It’s just down a steep embankment. Bring water shoes. The water, even in summer, is bracing.

Tapped Maple Rocker, ClearLake Furniture, Ludlow VT

FACTORY TOUR/SHOP: ClearLake Furniture

Vermont is known for its Master Craftsmen and handcrafted, hardwood furniture. And that’s what you’ll find in this superlative store/workshop.

Clearlake Furniture Factory Tour, Ludlow VT

Come in and owner, Brent Karner, will take you downstairs to witness all the work that goes into fashioning these pieces of art for the home. My favorite? A smooth, comfortable rocking chair made from tapped Maple trees. The tap holes remain and serves as conversation piece, for sure.

Blue Sky Trading Co. Ludlow VT

SHOP: Blue Sky Trading Company, Ludlow

This is a great browsing shop, with seemingly everything from jewelry to mugs to Vermont-made stuff. It’s been a favorite of many Okemo-goers since it opened in 1995.

Depot Street Gallery, Ludlow VT

If you’ve ever wondered about the afterlife of antique silverware, come to this crafts gallery. Here, see the many ways it can be fashioned into functional artwork and jewelry. Over 120 artisans are represented here – all from New England – and each with their own take on this Yankee-ful region.

Green Mountain Sugar House, Ludlow VT

STOP: Green Mountain Sugar House

On busy Route 100, stop in for some Vermont Maple Syrup and a super-duper, ultra smooth “Cremee” ice cream.

Fletcher Farm School, Ludlow VT

DO: Fletcher Farms School for Arts and Crafts, Ludlow

Vermont was once known for these “crafting” schools, which could be found all over the state. Now, just a few are left, including this one, on property once owned by Governor Allen Fletcher. (Fletcher also built the mansion now known as Castle Hill Resort).

So, while your brood is bombing down Okemo on mountain bikes or skis, you can study the fine art of Bob and Lace, Digital Photography, Basketry, Fiber Arts, Soap Making, Quilting. Or, choose from dozens of other craft and Fine Arts classes. Open daily in Summer, weekends in Fall and Winter.

Vermont Country Store, Weston VT

VISIT: Vermont Country Store, And More Stores Weston VT

On Route100, 10 miles south of Ludlow, you’ll find Weston, and in it, The Vermont Country Store, which is to this little burg what LL Bean is to Freeport Maine. It basically takes over Main Street with several retail shop buildings, Mildred’s Dairy Bar, and Bryant House Restaurant.

Even if your skin crawls at the thought of shopping, you will no doubt find something from your youth that reminds you of simpler times. (In my case, it was Silly Putty and that precursor to Nurf products, the plastic Lunar Launcher).

These kind of things, from penny candy to sock monkeys, are Vermont Country Store’s stock in trade. And the reason so many coach buses stop here.

Village Stores, Weston VT

But wait! Weston has other such shops, including the Weston Village Store, The Weston Village Christmas Shop and the tidy Village Green Art Gallery.

Teddy Store, at Hugging Bear BnB, Chester VT

VISIT: Chester VT

Take Route 103 about 12 miles to Chester – a sweet little town that locals say is inexpensive enough to be “up and coming” for new homebuyers (read: young people).

Around the Green, you’ll find two B&B’s – Inn Victoria, which serves afternoon Tea, and the Hugging Bear Inn and Toy Shop – for anyone mad about stuffed Teddies (they are all over the place – in each guest room, common rooms, and by the thousands on three floors in the Toy Shop).

Okemo Area Restaurants

Castle Hill Resort Restaurant, Proctorsville VT

EAT: Castle Hill Resort Restaurant

Though menu items are also available a la cart, opt for the three-course price fixe ($47-$65), which turns a good meal into a lingering experience. What is now the dining room was once the mansion’s wood paneled billiards room. Of course, you’re made to feel right at home.

The library has been updated with plenty of pretty silver grey seating, brightening up an otherwise dark space. In winter, start with drinks beside the vast fireplace that’s topped with original Tiffany sconces and plastered with field and farm themed tiles. Or, in warmer months, sip on the patio overlooking the surrounding mountains.

Beet Salad, Castle Hill Resort Restaurant, Proctorsville VT

Chef Alphonsus Harris has helmed the kitchen for over 20 years. He presents patrons – who sit at classy candlelit tables covered in linen and set with crystal wineglasses and china – perfectly cooked classic chicken, rack of lamb, and steak dishes. Service is warm and gracious. 

Willie Dunn’s Grill @ Okemo Valley Golf Club, Ludlow VT

EAT/GOLF: Willie Dunn’s Grille @ Okemo Valley Golf Club 

Some of the best mountain views can be found from the back patio of this little known golf-course-side restaurant. You don’t have to be a Golf Club member to wolf down great, fresh salads (I highly recommend the Cobb with candied bacon bits), burgers, and other elevated pub food.

MoJo Cafe, Ludlow VT

EAT: Locals also love Mojo Cafe for fast, casual Creole. Home Style Hostel for creative comfort food and craft cocktails. And The Downtown Grocery for great wine and mixed drinks.

Okemo Area Lodging

Castle Hill Resort Granite Exterior Proctorsville VT

STAY: Castle Hill Resort and Spa

What is now the Castle Hill Resort was first built, in 1901, as a summer home for industrialist Allen M. Fletcher (who was elected Governor of Vermont in 1912). The 10-room mansion, constructed in the “English Cotswold Style” of rough-hewn granite, was the first home in Vermont to be wired for electricity. As such, it’s on the National Historic Register, and a Historic Hotel of America.

Owners have lightly updated rooms and amenities for modern visitors. But Castle Hill retains its original beauty. On 100 landscaped acres, it sits atop a hill overlooking its sister property – The Pointe – below.

If you’re a rambunctious family, or are looking for a lower cost lodging, The Pointe, with motel-like rooms, is fine. But for something special – baronial even – stay in grand style at Castle Hill.

First Impressions of Castle Hill Resort

Angel Faces, Castle Hill Resort, Proctorsville VT

The approach to the stone mansion is impressive. It encompasses views of the 1889 Carriage House (that now serves as the Spa and Fitness Center), and a stunning stone pool area.

A walk around the manor yields some cool surprises, such as  literal “angels in the architecture.” Cherub faces adorn the intricately carved wooden trim around the roofline that lends Bavarian style to an otherwise English design.

Library, Castle Hill Resort, Proctorsville VT

Walk inside, and your eyes have to acclimate to the darkness of the polished paneled walls and 12 ft. high molded plaster ceilings. Fletcher went all out, apparently, with an eye for detail right down to the wallpaper (original) in the staircase that mirrors the design in the library ceiling. It’s posh and glamorous in a clubby, masculine way.

Rooms at Castle Hill Resort

Suite, Castle Hill Resort and Spa, Proctorsville VT

Every room is a “Man Cave” – dark paneled wood, fine fireplaces, and the comfiest of beds. All bathrooms are en-suite and have been updated.

Dining at Castle Hill Resort

See “Where to Eat” for Dinner coverage

Continental Breakfast, Castle Hill Resort, Proctorsville VT

For $9.95 per person, guests enjoy a daily Continental Breakfast in the gorgeous Oval Dining Room. There’s plenty available, including yogurts, granola, fresh fruit, freshly baked pastries, bagels, hard-boiled eggs and hot scrambled eggs.

Amenities at Castle Hill Resort and Spa

Pool, Castle Hill Resort, Proctorsville VT

The stunning saltwater pool (a quick walk across the driveway) is heated year round, and is especially popular après-ski. The poolside solarium is heated in winter and air conditioned in the summer. It’s where Yoga sessions are held. Hard tru tennis courts are located up the hill behind the pool. They are lit up at night for evening play.

Aveda Spa, Castle Hill Resort, Proctorsville VT

The Aveda Concept Spa and Fitness Center is right beside the pool in what was the mansion’s Carriage House. You can actually see original harness marks on the wood-slat walls, and stall doors leading into the dry sauna area.

Fitness Center, Castle Hill Resort, VT
Okemo Valley VT Pin

The fitness room – with state of the art equipment – features the original wood floor. The Spa is full service, with body treatments, hair, nails, and even couples massages. Room rates from $169-$299 include parking and wifi. Continental Breakfast an additional $9.95 per person.


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.