I have traveled through Bennington, Vermont, the southwestern entrance to the Green Mountain state, many times. Admittedly, however, I had never spent much time exploring Bennington. That is, until recently. My perception of the “gateway city to Vermont” changed dramatically after my stay at the Four Chimneys Inn. Four Chimneys is a historic Vermont bed-and-breakfast and was my home away from home for getting to known Bennington like a local. I love nothing more than exploring and learning to love new corners of our state.
Getting to Know the Four Chimneys Inn
Located just outside of downtown Bennington in the historic district of Old Bennington, Four Chimneys Inn is an elegant estate set on eleven acres. Its secluded location makes the property feel like a retreat. Yet, the inn’s location is in close proximity to museums, eateries, and historic Bennington icons. Pull up to the classic white exterior. Take in the elegance of the facade with four brick chimneys peaking out of the home, adding height and presence to the property.
The inn, dating back to 1783, is set away from the road with positioning among old-growth trees. When driving into the stately property, you can see the iconic Bennington Monument in the not-so-far distance. A large statue of a moose peeks out from the wooded edge of the property, adding a bit of whimsey to the grounds. Then step inside the iconic Vermont inn for history mixed with luxury, the perfect blend of comfort and sophistication.
The main living level of the Vermont inn has a cozy bar in the living room. Here, enjoy local spirits and beer and conversation with the barkeeper, who is also the innkeeper. The foyer leads into the elegant dining room, where breakfast is served. Open the lace-lined double doors and walk into the brick-floored, three-season porch. There you’ll find floor-to-ceiling windows, a beautiful chandelier, and furnishings that bring a pop of color into the common space. It’s the ideal space for a summery cocktail or snuggling up with a cup of coffee and a good book. The inn in its entirety is quiet, peaceful, and the perfect spot for respite.
Throughout the common spaces, you’ll find historic photos, showcasing the property’s historic. My favorite was a signed historic menu of Four Chimneys, featuring Gourmet Dinners and Entrees – the large majority from $3.95 to $4.95 for a meal.
The History of the Four Chimneys Inn
The original estate at Four Chimneys Inn dates back to 1783. Reverend David Avery, a pastor at the Old First Church just up the road from the inn, couldn’t keep up with the property. He sold it to Nathaniel Brush, a participant in the battle of Bennington. However, Brush ran out of money and turned the home into a boarding store and general house. Then in 1850, Tom Saxton from Troy, New York, purchased the property and brought it back to the grand state it had previously been in.
Unfortunately, thirty years later in 1910, the entire mansion burned to the ground. With only the foundation left, Philip Jennings rebuilt the estate and owned it until 1949. In the 1950’s, James Rollis turned the property into a fine dining restaurant, where Elizabeth Taylor and Walt Disney were guests, according to the inn’s history. In 2005, current owners Pete and Lynn Green, who were married at Four Chimneys Inn, traded their corporate lives in Boston for the quaint town of Old Bennington. Now, after restoring the inn to preserve much of the historic charm, they have created an inviting destination from which you can explore all Bennington has to offer.
The Accommodations at the Four Chimneys Inn
Four Chimneys Inn has 11 unique rooms to match their 11 acres, ranging from $139 – $429 a night. Two rooms can be found in out buildings for additional privacy. Using this comparison chart, you can determine which of the accommodations best suits your needs for your visit. Many rooms within the Vermont bed and breakfast feature refurbished hardwood floors, comfy couches for lounging, either gas or wood fireplaces, and jetted tubs or two-person showers.
We stayed in Room 1 just upstairs from the main entrance and foyer on the second floor. This Deluxe King room is lined with seven-bay windows overlooking the grounds, allowing copious light to pour in in the morning. The palette of soft blues and whites made for a sophisticated, yet welcoming space to unwind. The four-post Mahogany bed is the statement piece in the road, complemented by a gas fireplace with a television hidden behind the painting that sits above it. The bathroom, with an oversized jetted tub and standing shower, was expansive. Tea lights and bubbles are provided for the jet for the ultimate relaxation.
Once we settled into the room, we turned on the fire and enjoyed a local beer from Madison Brewing and some snacks. It was hard to want to leave for dinner in town. I could see us very easily coming back for a night of pure relaxation. The accommodations exude comfort, class, and genuine welcoming feeling of the accommodations.
Rooms on the third floor of the inn are cozier and for those wanting to experience the luxury accommodations on more of a budget. Room 7, an estate queen room, has a cute and cozy window seat looking out to the grounds. Rooms in the carriages houses, Room 8 and Room 9, have outdoor access and are more expansive inside. Room 8, the Ice House, is one of my favorite accommodations within the inn, accented with a brick wall, stone glass fireplace, and unique vaulted ceiling upstairs. The private room is two floors and would be perfect for an elopement or honeymoon.
Quality of Sleep at the Four Chimneys Inn
Wherever we stay, quality of sleep is one of the most important factors to us. After all, when you’re adventuring, you need restful hours of shut eye to prepare for more exploration the next day! The best part of our room at the Four Chimneys Inn was hands-down the bed. The natural foam mattress, made in Manchester, Vermont, features a helix air cell technology and exclusive hybrid memory foam that is supportive and pressure-relieving. Yet, you sink right in. The weight-response technology of the mattress responds to your movements all night long for a seriously good night’s night, which isn’t often the case at hotels, inns, and B&Bs.
Breakfast at the Four Chimneys Inn
Upon check in at the Vermont bed and breakfast, you’ll be asked to complete a simple form outlining your breakfast options in the morning. You’ll also indicate the time you’d like to dine in the sun-filled, simply elegant dining area. Four Chimneys serves a hearty, homestyle breakfast from 7:30am – 9:00am on weekdays and 8:00am – 9:45am on weekends. Coffee, hot tea, orange juice, apple juice, and V8 are offered for beverages. For entrees, you have the choice of:
- Four Chimneys Scramble: Three eggs scrambled with bacon crumbles, local farm cheddar, sweet peppers and onion. It’s served with bacon, potatoes and wheat toast.
- Fruit Cup with Vanilla Yogurt Granola: Served with an oat-bran muffin.
- French Toast with an Orange-Scented Blueberry Cream Cheese Drizzle: Served with maple sausage and fresh fruit.
- Buttermilk Pancakes with Vermont Maple Syrup: Served with maple sausage and fresh fruit.
- Oatmeal with Raisins and Brown Sugar: Served with wheat toast and fruit
- Bacon Egg and Cheese Bagel: Served with breakfast potatoes.
The innkeepers ask you to make note of any dietary preferences and restrictions and are happy to customize meals. We opted for the Bacon, Egg, and Cheese Bagel (simple but so good) and the French Toast, which was an art form. It was one of the most beautiful, artfully designed breakfasts I’ve had at an inn in Vermont. Both meals filled us up for a day of adventuring in Bennington.
Where to Eat in Bennington, Vermont
When we checked into Four Chimneys Inn, the innkeeper, Kim Johnson Turner, was raving about Allegro Ristorante, an Italian eatery in downtown Bennington. Reservations are recommended at Allegro, and the menu ranges from crispy calamari, gnudi with bacon and peas, and rabbit and ricotta sausage meatballs for starters to Papparadelle with Bolognese, Fettucine with Marinated Skirt Steak, and Sausage and Broccoli Rabe for entrees.
Wanting something a bit more casual and specializing in beer, we decided to cozy on up at the bar at Madison Brewing Company for dinner. The large restaurant has extensive seating upstairs and done. The food options are extensive from burgers, sandwiches and salads to Smokehouse Mac N Cheese, Pork Schnitzel, Yankee Pot Roast and other more filling meals.
We shared Maple Chipotle BBQ Wings followed by The Brewhouse Burger, certified Angus beer, smokehouse cheddar, crisp bacon, and balsamic glazed onions, and a Buffalo Salad with field greens, crispy chicken, pico de gallo, avocado, cucumbers, bleu cheese crumbles, and tortillas crisps. The food and Vermont craft beer both exceeded our expectation after a day adventuring.
The Blue Benn is an iconic roadside eatery. The diner, featured in Classic Diners of Vermont. a must for the role it has played in the local community it serves. The food is also outstanding. They offer more vegetarian and gluten-free offerings than many diners in Vermont, and there’s always a line to get in. Check out the menu from above the bar and people watch as regulars come and go throughout the day. The Blue Benn is cash only.
Tips for Visiting Four Chimneys Inn Like a Local:
Are you traveling on business Sunday – Thursday? If so, inquire about a corporate rate for your stay.- Most Saturdays (and Fridays) require a two-night minimum. However, give the inn a call directly to see if they can make an exception for your visit to Bennington.
- Staying at the inn for a special occasion? Check out their enhancements to your stay: Local Craft Beer Snack, Cheese and Cracker Plate, Mini Birthday Cake, Fresh Seasonal Bouquet, Vermont Snack Basket, etc.
- Wondering about accessibility? For an inn structure built in 1931, there have been many upgrades undertaken to make the inn accessible to all guests. Call the inn directly to inquire about the room best suited for you.
- Renting the whole estate is possible for a family reunion or wedding event. Call to inquire about availability and making Four Chimneys Inn a gathering place for your friends and family.
Interested in visiting Four Chimneys Inn and Bennington, Vermont? Pin this content for your next Southern Vermont adventure!
21 West RoadBennington, VT 05201
802-447-3500
innkeeper@fourchimneys.com
*Travel Like a Local: Vermont received a complimentary stay in order to honestly review the inn. All thoughts are our own.
Categories: Destinations