It has always been a dream of mine to take a roadtrip in New England during autumn. Like many, fall is my favorite season (unless you count Christmas as a season!) and the changing leaves, hills, and charm in the Northeast just can’t be beat. I recently had the opportunity to finally explore the world-renowned foliage, this year in Connecticut and Vermont, and it was everything I’d hoped it would be and more!
Whether you’re already located in the Northeast or looking to visit, keep reading for the perfect itinerary (and more details below) for your fall getaway!
Itinerary Overview
Day 1: Litchfield, CT
MORNING:
» Enjoy breakfast at Toast & Co.
» Choose 1 or more of CT’s fall foliage-viewing driving routes
AFTERNOON:
» Head downtown to wander shops and sights
» Lunch at Market Place Tavern
» Stop for ice cream at Arethusa Farm Dairy
EVENING:
» Dinner at Community Table
Day 2: litchfield, CT
MORNING:
» Grab coffee and breakfast sandwiches at Arethusa a mono
» Hike at Bear Mountain, Steep Rock Preserve, or Mt. Tom State Park
AFTERNOON:
» Visit Thorncrest Farm for gourmet, milk house chocolates
» Stop by The Dutch Epicure for meats, cheese, and condiments (with the chocolates, of course) before heading to a local vineyard
EVENING:
» Enjoy prix fixe dinner experience at Winvian Farms
Day 3: woodstock, VT
MORNING:
» Eat breakfast at Soulfully Good Cafe
» Walk around downtown and explore boutiques
AFTERNOON:
» Grab lunch on the road and begin driving VT’s famous Route 100 highway (also consider combining with historic covered bridge tour)
EVENING:
» Visit Simon Pearce gallery to shop and dine-in / take-out dinner
Day 4: woodstock & stowe, VT
MORNING:
» Grab breakfast at Mon Vert Cafe
AFTERNOON:
» Take a day trip to Stowe; stop at Cold Hollow Cider Mill on the way
» Explore downtown Stowe (don’t miss the picturesque Stowe Community Church – stop in Salon Salon’s parking lot to get the best photos!)
EVENING:
» Dinner at Red Rooster, located within the Woodstock Inn
Where to Stay
When visiting New England during peak season (late September through early November), you can almost always expect to compete for hotel availability and increased prices. I’d highly recommend planning your trip at least a few months in advance, especially if you’re trying to stay close to downtown. Airbnb would also be an excellent option!
In terms of which month or week to plan your trip, check out CT’s fall foliage map for where and when peak viewing is estimated to occur!
Litchfield
The Litchfield Inn was a beautiful and (relatively) affordable hotel. It’s expansive front lawn was matched with a colorful tree-lined courtyard in the back complete with firepits and a garden, which was the perfect place to relax and enjoy a glass of wine before dinner! It was also very centrally located to downtown, restaurants, and parks.
Woodstock
We were so excited to stay at The Woodstock Inn, which was equally as beautiful outside as it was inside. It was situated in the heart of downtown and walkable to every shop and restaurant. What we probably loved most was their cozy lobby, which had numerous (socially distanced) seating areas and a roaring fire at the front.
Where to Eat
Unsurprisingly there were no shortage of cute restaurants and cafes in town! Here are some delicious eateries where we ate or were recommended:
Litchfield
- Toast & Co: local breakfast restaurant known for speciality toasts and breakfast sandwiches
- Arethusa a mano: super popular, and for good reason – delicious pastries, breakfast sandwiches, and coffee drinks
- Market Place Tavern: we didn’t get a chance to dine here but one of the most popular places downtown offering delicious comfort foods
- Community Table: probably our favorite meal from the trip – everything from the atmosphere, to the cocktails to farm-to-table style food was perfect!
- Arethusa al tavolo: romantic American/Italian restaurant with beautiful courtyard
- ORE HILL & Swyft: another recommendation that we didn’t have time to visit, this highly raved dual-restaurant offers two separate dining experiences
Woodstock
- The Red Rooster: conveniently located in the Woodstock Inn with a sophisticated dining atmosphere (we ate both in the restaurant and ordered room service for a lazy night in!)
- Soulfully Good Cafe: serves breakfast and lunch with organic, local ingredients
- Mon Vert Cafe: we ended coming here both mornings, it’s that good!
What to do
As most of our trips are nonstop sightseeing, we were especially looking forward to a slow-paced long weekend focused on leisurely driving and spontaneously exploring what each town had to offer. Locals were kind to offer some great suggestions, and we also did a little research on some top-rated activities.
Litchfield
- Hike: there are no shortage of trails to choose from; we really enjoyed the hike to the Steep Rock Preserve summit – the views were stunning and it was the perfect balance of leisure and challenge.
- Thorncrest Farms: a definite must-see is this local dairy farm; in addition to milk and yogurt they sell the most AMAZING chocolates, of any type and combination you could imagine! The line can move slow but it is well worth the wait.
- Wine tasting: we were surprised to find so many vineyards in the surrounding towns (Sunset Meadows, Miranda Vineyard, and Hopkins Vineyard, to name a few). Sunset Meadows was only about 10 minutes away from our hotel, allows pets, and has an expansive lawn for guests to sit, eat, and drink at their leisure. Before enjoying a wine tasting, be sure to stop by The Dutch Epicure shop to pick up some meats, cheeses, crackers, and snacks!
Woodstock
- Shopping: downtown Woodstock is full of charming, unique boutiques; you’ll also definitely want to check out the Simon Pearce glass and pottery gallery (in neighboring town of Quechee).
- Scenic Drives: whether you choose one of VT’s many scenic driving routes, or make a day trip to a nearby town (highly recommend Stowe!), any time on the road will offer beautiful sights.
- Sugarbush Farm: a must-visit for incredible views alongside the most delicious syrups, cheese, and other maple products.
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