A Complete Weekend Guide to Manchester, Vermont in the Fall

October 11, 2020

Vermont in the fall is something special. It’s true, the entire state has so much to offer when it comes to leaf peeping, but nestled in the Taconic Range is Manchester. A quiet area with the perfect balance of town and country. I’ve been to this area of Vermont three times, each time was in the fall and each time was a little different. But nonetheless, idyllic.

Where to stay

I have now stayed at Hill Farm Inn three times. So, one would say I really like it there. It’s in the town of Sunderland, but you probably know the neighboring town of Manchester a bit better. It is a quintessential Vermont town complete with picturesque mountainous landscapes, skiing delicious restaurants, local artisan shops, Vermont roasted coffee shops, maple syrup shops and the list goes on.

More on that later, back to Hill Farm Inn. This boutique inn is right on the Battenkill and at the base of the Taconic Mountain Range in Equinox Valley. The property has an event barn, heated saline pool, hot tub, fire pit and covered porches. The surrounding meadowland has a mile-long walking trail along the Battenkill River, and space for our animal friends like alpaca and two cats (Tiger and Maple Mae) to roam.

History of Hill Farm

This history of the farm goes back 200 years. In 1774 Sunderland was organized by a group of Connecticut homesteaders, led by Ethan and Ira Allen. Among them was Abner Hill who, in 1799, bought and built on the land that Hill Farm Inn sits on today. Then, it was a dairy farm and today it is an inn that sits atop 50 acres. The Pollard family stumbled on the property when they were entertaining the idea of buying property in Vermont for long weekends and vacations. When they visited, they just couldn’t say no. Instead of having it as a family home, they opened the inn for all to enjoy.

Today, the footprints of the 1790 House and the Main Inn from the dining room threshold forward, and the barn are all of the original structures. The barn was made in two sections, late 1800s and early 1900s and has since been lovingly restored.

The Hill Farm Campus

The Main House of the inn, where I stayed, is the hub. The building dates back to 1830 and that charm is still alive. The first floor, where you check in, is the space for gathering. There is a spacious dining area, library space with a pool table, living space with a fireplace and rocking chairs on the wrap around porch. Hill Farm also has a full liquor license so there is an on-site bar for guests to enjoy. Wine by the fire, anyone?

vermont in the fall

The second floor is where the seven guest rooms are. There are five queens and two kings. I’ve stayed in a variety of the rooms, first the Battenkill, second the Honey Bee Suite, and third Saratoga. I can’t pick a favorite room because they are, seriously, all so beautiful AND I was in great company on each visit- which made it that much sweeter. The Battenkill is known as their ‘honeymoon’ room. It has valley views, handcrafted four poster king bed, and lots of space. The Honey Bee Suite overlooks the surrounding mountains, has an adjoining sitting area separate from the bedroom, and the cozy queen bedroom. Saratoga also has mountain views with equestrian inspired décor. This was the smaller of the three but I loved returning to this cozy space after a day of leaf peeping.

There are also three cottage style accommodations. The 1790 House has four bedrooms, a common area, coffee bar, covered porch, and patio.  The four rooms are available to book separate or as a group rental. The Farm House sits on the other side of the inn and is a vacation rental through and through. It’s perfect for longer stays for a group of 6 or a family. There are three second- floor bedrooms, one full bath, and a trundle bed downstairs. The Madeline, located across the road, is the ideal spot for families and groups. It was built in the 1930s and was renovated to accommodate six.

Where to eat in Manchester

With Hill Farm Inn being a stone’s throw away from Manchester, there are loads of delicious bars and restaurants to eat (and drink) at within a 10 minute drive. A trip to Vermont in the fall would not be complete without delicious food and drink.

Silver Fork– Located in a beautiful old Library in Manchester with massive floor to ceiling windows, walls filled with mid-century art, and a delicious menu infused with Asian and Spanish flavors. Reservations required.

Copper Grouse– Part of the Taconic Hotel but definitely not your average hotel cuisine. The lunch and dinner menu have so many delicious offerings like crispy Brussel sprouts in mulled cider, hot honey half chicken, and the butternut ravioli. Enjoy it all al fresco on their outdoor patio. Reservations required.

Zoey’s Deli– The perfect grab and go sandwich and salad spot.

Firefly– Taproom and tapas! More of a relaxed environment.

Seasons– Open for lunch and dinner this spot offers American fare. Outdoor patio seating, too! Reservations not required but recommended.

Bonnet & Main Café The coffee shop attached to Northshire Bookstore. They offer some takeaway breakfast and lunch options with seating inside and outside. Best cold brew in town, in my most humble opinion.

What to see + do in Vermont in the fall

Take a drive up Equinox Mountain

Hiking Equinox, the tallest in the Taconic Range, is an option but we decided to have a relaxing day (a rarity) and drive up so for us it was worth it to spend $25 ($20 per car and $5 per additional passenger).

This road is the longest, privately owned, paved toll road in the United States. From the summit, you can see several surrounding ranges in the distance like the Catskills, Adirondacks and the Berkshires. Once back down, visit the nearby Equinox Nursery to fulfill all of your Vermont in the fall, corn maze, pumpkin, hot cider drinking dreams.

summit of equinox mountain in vermont

Visit the different art galleries

There are a lot of different artists in the Manchester area. From stained glass to glass blowing, contemporary to abstract realism, wood working to sculpting- there’s a lot going on. I recommend popping into The Norman Rockwell Museum, the Sugar Shack for a Norman Rockwell exhibit and dedication, Epoch Gallery, Johnny Hinrich’s Studio, and Manchester Hot Glass.

Hike up Stratton Mountain

This is a 7.6 mile, heavily trafficked out and back trail about 45 minutes from the Hill Farm Inn. The trail isn’t too steep (1,751 elevation gain over 3.3ish miles) and is well marked all the way up. Part of it joins in on two long trails, the Appalachian Trail and Vermont’s Long Trail. There’s not much of a view unless you climb the fire tower, up there you can see endless views of the surrounding mountains.

As mentioned, this is a heavily trafficked trail- mostly because there is gondola access via Stratton Mountain Resort. I recommend getting there as early as possible to avoid crowds, otherwise you’ll be waiting behind 20 people to climb the tower.

Hot tip: if you’re coming from Hill Farm Inn there are two ways to access the trailhead. One way clocks in at just under an hour and the other is 37 minutes. We opted for the shorter route and ended up on a beautiful, fall foliage lined dirt road that winds up the mountain.

Find Red Covered Bridges

At this point, I might be a connoisseur of red covered bridges. Two of my favorites in the Manchester area are the Snow Covered Bridge on Stratton Mountain and Chiselville Bridge. You can find more in this article.

Day trip to Sleepy Hollow Farm

Probably one of the most photographed, working farms in the U.S. providing the most quintessential Vermont in the fall photo! Not kidding. I remember seeing this all over Instagram last fall so I had to add it to my itinerary. The farm dates back to the late 1700’s but today its owned by Aerosmith guitarist, Joe Perry. You can read more about the history of Sleepy Hollow Farm here.

Sleepy Hollow Farm is about a 1.5 hour drive from Manchester and located on Cloudland Road in Woodstock.

sleepy hollow farm in vermont

Visit Queechee Gorge

I recommend adding Queechee Gorge onto your day trip itinerary when visiting Sleepy Hollow Farm. The gorge formed around 13,000 years ago by glacial erosion and today the Ottauquechee River flows through it. There’s a couple of turnoffs on each side of the bridge you can turn into to park. Walking along the bridge gives you stunning views of the gorge and river 165 feet below.

queechee gorge in vermont


A Complete Guide to Manchester, Vermont in the Fall


Loved this site! So glad I found it.