Last Minute Fall Vacation
I am taking a break from Interior Design topics to share with you an incredible leaf-peeping journey in Vermont and inspire you to create this experience for yourself at the spur of this Fall 2023 moment! It’s a must to experience the most spectacular Autumn in the US just once in your life if not multiple times as we have had the privilege of doing.
Places to Visit in Vermont
For first timers, Vermont may be daunting to navigate and with all the adorable and charming towns, how do you know where to start? I will share everything with you from booking your flights to traveling the southern part of the state including places to stay, wine, dine and shop.
Last year on October 1st, I woke up with a deep yearning to be there, as if I couldn’t live without it. By the time we retired for the evening, this itinerary was planned and booked, and 10 days later, we were off! Perhaps you’ll be twitterpated to do the same.
There are several ways to shake this tree, but I will only cover one itinerary as it became our favorite over the period of time we lived in New England from 2013-2020.
First, TIMING is everything. I recommend sometime between October 8 and 16th to fully narrow it down.
Fly into Bradley International Airport in Windsor Locks, Connecticut. (See, now you have the answer to that question!) I recommend taking the last flight out in the evening, spending the night in an airport hotel, and rising fresh the next morning ready to hop in a rental car and head north.
Towns in Vermont
Bradley Int’l Airport
To Vermont Towns in order:
-Brattleboro
-Grafton
-Chester
-Arlington
-Woodstock, VT
-Arlington/Manchester
Towns in the Berkshires
-Great Barrington, Mass
-Stockbridge, Mass
-Lennox, Mass
Start by taking in the scenery on the way to your first stop: The funky New England town of Brattleboro.
Have lunch at the art-laden Superfresh Organic Cafe and then enjoy meandering down Main Street where you’ll find an incredible selection of colonial antiques, vintage clothing, and privately owned boutiques. Shop for LPs at Turn It Up. And don’t forget to pause and breathe in the crisp New England air, free of big city pollution! Make sure to visit Mocha Joe’s and try their heavenly pumpkin spice latte. When you taste the latte and experience the vibe there you’ll never look at Starbucks the same way again.
Traverse the Creamery Covered Bridge on your way to your next stops: Chester and/or Grafton. Both lovely, but small towns are worth a quick visit before you retire at the Arlington Inn outside of Manchester.
As you are traversing between towns, don’t be afraid to abandon the GPS and explore hidden roadways for surprise views and photo ops. It’s the point of the trip, leaf peeping! These photos are unedited.
The Arlington Inn is centrally located for a northern excursion to Woodstock and southern access to The Berkshires. When we walked into this Inn we were welcomed by a friend of the owner. Her desk, complete with a colonial hand bell, was situated in a grand historic foyer with a wood carved staircase and reading rooms furnished with period antiques to the right and left. We loved our historic room, the kind service, and the lovely breakfast served in the atrium.
On your first morning at the Arlington Inn, take in the breathtaking drive up to Woodstock, Vermont’s most beautiful town, and spend much of the day there. Alternatively, if you have the luxury of planning a longer trip, there are many historic places to stay in Woodstock where you can spend a night and take in more of the town.
On your second morning after checking out of the Arlington Inn and enjoying its quaint breakfast, you’ll be heading down to the Berkshires in Massachusetts. Though leaving Vermont, this, for me, is the best part of the trip and a great finale to your stay! It also takes you back in the direction of Bradley International Airport completing your circle for your flight home. Make sure to book your return trip late in the day so that you can enjoy the full landscape of the Berkshires. I recommend these three towns nestled together with some fabulous finds in each: Stockbridge, Lennox, and Great Barrington.
Great Barrington is the largest of the towns and its Main Street is brimming with gorgeous home goods & apparel shops, cafes, wine bars, and bistros. We always enjoy GB Eats for a good sandwich and pastry. Don’t miss the coffee at Fuel or meandering down side streets to enjoy hidden gems like GB9 apparel.
As evening draws near, your next adventure begins when you check in to The Red Lion Inn.
This hallmark hotel of the Berkshires is famous for its haunting and history. Even if you don’t like ghosts and choose not to stay there, pay a visit and take a tour of the colonial decor, lounge in the lobby, or read in the reading room. Most importantly, your entire New England stay will not be complete without an evening of drinking and listening to live music in their cool bar venue: The Lions Den. We planned our whole trip so as not to miss The Lion’s Den and our favorite Fall Cocktail: Apple Cider and Rum in a glass mug with a cinnamon stick. Between the bewitching red vibe and warm drink, we are transported to another world for an evening in a season we wish would never end (the Red Lion Inn books up quickly in the Fall, so if you can’t get a room, stay at The Constance Inn, a nearby colonial inn in the countryside of Lennox).
Cider and Rum Cocktail Recipe:
In a glass mug, mix
- 8 oz of hot apple cider
- 1 to 1.5 oz of rum according to preference
- Stir with a cinnamon stick and leave it in for flavor
- Add a few apple slices if desired
- Sip and sink into Fall bliss!
Every time I serve this cocktail to my friends back home it’s a huge hit!
New England charm is always replete with cobblestones and cafes. The next morning we recommend you visit a novel little cafe just a couple doors from the Red Lion Inn. I could not track down the name, but see the photo here and walk to the left of the Inn and you will find it nestled next to the General Store.
Spend the rest of your time strolling through Stockbridge and Lennox, and then plan to head to the airport, sort through all your photos on the airplane, and revel in the beauty of your experience while telling yourself you’ll be back next year. I hope this article has inspired you to go, taste, and see this Fall wonderland for yourself. It’s not too late to plan it, so start reserving and have a wonderful trip!
For more topics on Interior Design, Travel, and all things Creative, visit my Liz Gabriel Interiors Blog page. For monthly “new on the blog” posts, subscribe to my monthly newsletter!