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Covered bridges are the reason people travel to Vermont.

10 Things I learned on a Vermont Road Trip

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By the Backseat View

Mount Mansfield is a top thing to do in Vermont
Mount Mansfield

Vermont is stunning, from storybook towns built in the 1800s to mountain views, waterfalls, and dramatic gorges, with a friendliness and sense of community that seems to follow you down every little country road. And foodies, plan your trip hungry. Come for the different colors of maple syrup that’s tucked into everything from breakfast to ice cream.

Vermont Road Trip

Bingham Falls Trail is a top thing to do in Stowe, Vermont.
Bingham Falls Trail

Vermont Travel Guide

Fill your dreams with smoked cheese, maple butter, and an apple cider slushie with maple ice cream topped with apple donuts, rightfully called a Dreamie. You visit Vermont for the legendary fall colors, but you’ll come back for the perfection of it all – the covered bridges, mountain roads, tiny villages, waterfalls, maple everything, and those little unexpected moments that make you slow down and say, “Now THIS is Vermont.”

Welcome to Classic Americana.

Quechee Bridge is a top attraction for visitors to Vermont.
Quechee Bridge

Iconic Things to do in Vermont

After we go over the highlights, I’ll give you my exact itinerary and planning thoughts. 10 Things I learned on my Vermont Road Trip are just the beginning, you know I learned more.

  • Green Mountain National Forest – Forested peaks and scenic trails in southwestern and central Vermont. The most notable aspect is Route 100, which runs parallel to the forest. Lye Brook Falls is a 125-foot cascading waterfall.

Lake Champlain

  • Lake Champlain in Burlington– Waterfront views and recreational opportunities like boat tours. To be clear, I saw that it was called the 6th Great Lake, so my expectations were too high. The first thing I learned was every view I had of the lake was murky, brownish, and very lake-like. I’m sure there are days it’s bright blue, but I wasn’t knocked speechless like I was with the Great Lakes.
Lake Champlain is a top thing to do in Vermont for readers of the Vermont Travel Guide.
Lake Champlain

Ben & Jerry’s

  • Ben & Jerry’s Ice Cream Factory – A sweet stop in Waterbury with tours. The tours are every 30 minutes and cost $6 a person. 2nd learning opportunity was that the tickets are released two weeks in advance and sell out quickly. I thought we could just walk up and join the next tour.
Ben & Jerry's Ice cream tour is a famous stop for readers of the Vermont Road Trip.
Ben & Jerry’s

Cold Hollow Cider Mill

  • Cold Hollow Cider Mill– This place is across from Ben & Jerry’s with the best apple donuts, maple creemees, and apple slushies. They put it all together and call it a Dreamie. 3rd thing I learned is a Dreamee is THE BEST thing you will eat, probably ever. Personally, I got another donut with mine so I could have the hot-and-cold experience until the very end of my slushie. Think Apple Barn type experience for my Gatlinburg friends.
Dreamee is a top thing to eat in Vermont for readers of the Vermont Travel Guide Road Trip.
Dreamee

Shelburne Museum

  • Shelburne Museum – It has a steamship, working circus carousel, an authentic fully stocked General Store, a carriage barn filled with vintage horse and buggies, and 25 historic buildings filled with collected art. It’s like a trip back in time. For number four: I learned that the Ticonderoga is the last walking beam side wheel passenger steamer in existence. I felt like I was touring the Titanic soaking in the Gilded Age Glamour.
The Shelbourne Museum is a top thing to do in Vermont.
Shelbourne Museum
  • Vermont State House – A historic golden-domed capitol in Montpelier. The capital is small, with a nice walkable downtown filled with vintage shops for an hour-long stop.
Vermont's capital is an iconic part of a Vermont Road Trip.
Vermont Capital
  • Kingdom Trails – Renowned mountain biking and hiking network of over 100 miles of trails in the Northeast Kingdom of Vermont.
  • Hildene– Lincoln’s family home with 412 scenic acres. It’s located in Manchester and 90 minutes from everything in my itinerary.

Quechee Gorge

  • Quechee Gorge – Often called Vermont’s “Little Grand Canyon.” For number 5: you literally drive over the gorge on the main road. There’s no hiking. People were hiking down to the water. The Quechee Club is the premier golf course, so rent a house in the community with access if you want to golf. I came to Quechee for Simon Pearce.
Quechee Gorge is top thing to do in Vermont for travelers of the Vermont Road Trip.
Quechee Gorge

Simon Pearce

  • The Simon Pearce glass shop, which was the glass shop in the movie Sweet Home Alabama. For # 6, I learned that Simon Pearce is one of my favorite stops in Vermont. Maybe it’s the waterfall and covered-bridge view, the stunning glass pieces being made, or the restaurant that made me love this unique place.
Simon Pearce is world known glass blowing shop in Vermont.
Simon Pearce
Simon Pearce is an educational and beautiful hidden gem in Vermont.
Simon Pearce
  • Maple Creemee– The soft serve ice cream is everywhere, but don’t forget those maple crunch toppings. Number 7 for things I learned is that the maple crunches make the flavor pop.
Maple Creemee is literally the Vermont dessert.
Maple Creemee

Hidden Gems of Vermont

  • Stowe Recreation Path – 5-mile scenic biking and walking trail that ends with a covered bridge. The 8th learning opportunity is the Stowe Recreation Path is how you experience the REAL, peaceful side of Stowe.
Stowe Recreation Trail is such a peaceful experience for travelers to Vermont.
Stowe Recreation Trail
  • Mad River Valley – Covered bridges and mountain views. These are charming little towns along Route 100 like Waitsfield, Warren, and Fayston. You can float the river or Blueberry Lake or hike limitless trails. Moss Glenn Falls is in Granville.

Sugar Bush Farm

  • Sugar Bush Farm-If you want to see trees tapped for maple syrup and eat the best smoky cheese of your life, this is your invitation. Lesson # nine is that maple trees look like they are getting IV’s while collecting syrup.
Sugar Bush Farm is the perfect way to connect to REAL Vermont for readers of the Vermont Road Trip.
Sugar Bush Farm
Maple trees are the symbol of Vermont, so all travelers want to see how syrup is collected.
Maple Tree
  • Grafton Village – Preserved 19th-century charm.

Flume Gorge

  • Flume Gorge– is located in Franconia Notch State Park and requires a timed ticket. If you are traveling in the spring with high water levels, don’t miss this! There are several fantastic hiking trails, like Artist’s Bluff Trail. Echo Lake is 1,931 feet above sea level. However, I’ve been to this area before, so I know these “easy” trails involve climbing over rocks and going uphill. The Flume Gorge hike is 2.2 miles and easy enough. Technically, this is in New Hampshire and 45 minutes from the Vermont line. However, I love it, and I don’t want you to miss it. So visiting the Flume Gorge is my 10th lesson learned: waterfalls, rocks, river views, a covered bridge, and a sparkling pond.
The Flume Gorge is a beautiful natural attraction,
Flume Gorge

The Vermont Teddy Bear Factory

  • The Vermont Teddy Bear Factory is the largest maker of handcrafted American-made teddy bears in the U.S. Tours are $6 a person and after watching teddy bears be made, you visit the Teddy Bear Hospital. It’s stuffed animal heaven and it’s going to cost you $50 to buy a new best friend.
  • Plymouth Notch- Home to Calvin Coolidge, located near Woodstock.

Best City to Visit in Vermont

Burlington

Located on Lake Champlain, Burlington blends a vibrant arts scene with outdoor access and lakefront beauty. Lake Champlain Chocolates are some of the finest confections in the country. The Shelburne Museum is 10 minutes outside Burlington and offers a walk through history.

The Shelbourne Museum is a top thing to do in Vermont for readers of the Vermont Road Trip.
Shelbourne Museum

Best Small Towns in Vermont

Vermont has a 251 Club for visiting every town in Vermont. There’s also a 100 Covered Bridges Club if you want to spend the summer in Vermont.

Stowe, Vermont

Known for alpine scenery, classic inns, and outdoor activities, Stowe captures Vermont’s postcard-perfect charm. Stowe doesn’t feel “real.” It’s like you have entered a Hallmark movie. It’s my favorite of the 25 towns we visited in Vermont. After a few hours in town, Stowe continues to impress you with Bingham Falls, the gondola up Mount Mansfield, the rocks at Smuggler’s Notch, the Von Trapp Lodge views, and the Stowe Recreational Path. Stowe also has a fantastic food scene.

Stowe has a nice welcome photo spot for everyone's Instagram.
Stowe Sign
The history in Stowe is what gives the town character.
Stowe’s Church
Stowe has the best character homes to travelers to experience.
Stowe
The General Store has the cutest shops in Stowe
Stowe General Store
Stowe has adorable homes for readers to visit.
Stowe Home
Vermont is known for covered bridges.
Stowe Bridge

Woodstock, Vermont

The wealthy in New America designed a perfect town in 1761. It’s Woodstock. Their vision to save it from commercialism and preserve the original homes is genius. Woodstock is frequently named one of the prettiest small towns in America, so everyone agrees it’s perfection. It’s walkable, filled with boutiques, flowers, and covered bridges.

Woodstock is famous for its historic homes.
Woodstock home
Woodstock is famous for the homes so readers of the Vermont Travel Guide Road Trip want to see the homes.
Woodstock Home
Woodstock is famous, and readers want to see the town.
Woodstock
Covered bridges are what makes Vermont, it's why people come.
Woodstock Middle Bridge

National Historic Park

You can walk to the Billings Farm & Museum and Marsh-Billings-Rockefeller National Historic Park, which share a partnership with the same entrance. It’s easy to spend a few hours visiting a historic dairy farm and cross the street to see the three mansions and explore the 550 acres of forest trails. Honestly, it’s in the title but I missed that this was a pay to tour the mansions type National Park. The $13 tour reservations are released 60 days in advance at Recreation.gov.

Billings Farm Museum and National Park is a top thing to do in Woodstock for readers of the Vermont Travel Guide.
Billings Farm Museum

There is a magical feeling in the air in Woodstock. The chiming of its six historic church bells serves as a beautiful reminder that you are simply passing through.

Stowe VS Woodstock

So, if you are trying to decide where to spend more time between Stowe and Woodstock. Stowe has the better restaurants and natural experiences. Woodstock has more impressive historic houses and better shopping.

Best Vermont Nature Experience

Green Mountain Forest

Miles of trails, scenic drives, and quiet wilderness define Vermont’s natural heart. A few of my favorite stops are Bingham Falls, Moss Glenn Falls, Lye Brook Falls, and Smuggler’s Notch. Deer Leap Overlook is a 3.2-mile loop with dramatic cliffside views.

Hikes have lots of rocks and travelers need to be aware.
Vermont trails

Best Animal Encounters

Moose

  • Moose & deer in the northern regions –Moose Alley (Route 105 & Route 114): the 15-mile stretch of Route 105 between Island Pond and Bloomfield is legendary for roadside moose sightings.
  • Route 114 between East Burke and Canaan is equally famous at daybreak and sunset. Moose Bog off Route 105 is a 0.5-mile trail to a viewing platform where moose frequently feed.
  • I have a friend who went on a moose tour in NH and loved it. Pemi Valley Moose Tours and Gorham Moose Tours have a 90% moose sighting success rate.
  • Vermont Reindeer Farm – Visits in West Charleston by appointment only, located in Northeast VT near the Canada line. Who doesn’t want to attend reindeer school?

Unique Vermont Experiences

  • Tasting fresh maple syrup –different color syrup for collecting at different temperatures
  • Visiting covered bridges-there are over 100 bridges
  • Experiencing fall foliage with scenic byways
Covered bridges are the reason people travel to Vermont.
Taftsville Covered Bridge

Best Time to Visit Vermont

  • September to October is peak foliage season, bringing the biggest crowds and grid locked roads.
  • Summer offers mild weather for hiking, biking, and low crowds. I went the end of August/first of September and it was perfect.
  • Winter is ideal for skiing.

How long do you need in Vermont?

4 Day Itinerary

This is a basic itinerary that hits the highlights, but I will give you the hourly breakdown for an August trip next. Arrival and departure days don’t count in this plan. You will need twice the time during peak leaf season.

Day 1: Burlington
Explore the Lake Champlain and Church Street downtown, then the Shelburne Museum.

Day 2: Stowe
Hike to Bingham Falls, ride the gondola up Mount Mansfield, drive Smugglers Notch, visit the Scottish Highland cows at the Von Trapp Lodge, take the Stowe Recreational Path for a bike ride, and visit local shops.

Day 3: Green Mountains
Drive scenic routes and explore forests and charming towns on Route 100. Waterbury for The Cold Hollow Cider Mill with Ben & Jerry’s across the street, the gold-domed capital, and Sugar Bush Farm for smoky cheese and syrup.

Day 4: Woodstock with the Quechee Gorge & Grafton
Walk historic Woodstock, Quechee Gorge, Simon Pierce, Billings, and the Rockefeller National Park across the street.

Woodstock buildings have so much personality.
Woodstock

7 Vermont Itinerary Decisions

  • Decide on flights into Burlington or Boston. Boston was $400 cheaper. However, plan an hour to pick up a rental car. Boston has you standing on a packed, Disney-type bus for 30 minutes with your luggage, making multiple bus and train stops before you reach the rental car center. Seriously, Boston, build a SkyTrain. Atlanta can teach you.
  • Pick your must-dos. For me, that was Stowe, Woodstock, Simon Pearce, Cider Hollow Mill, Bingham Falls, and driving Route 100.

Why to Avoid October

  • Decide on the time of year. Everyone comes for fall, but the traffic on Route 100 is a nightmare. Restaurants are booked months in advance, and hotel prices double, so I chose early September. Route 100 is a two-lane rural highway with average speeds of 50 mph except in October, when it drops to 10 mph. What took me an hour to visit a few towns can easily take eight hours in October because it gets gridlocked.

Loop Itineraries

  • Realize that you are probably making a loop with your itinerary, so don’t travel the same road twice. Burlington flights start in the north, travel south, then back to Burlington. Boston flights start in the south and travel north, then back to Boston. That’s how I ended up at the Flume Gorge, swinging out to a different road.
  • Next, add the hidden gems and fill in the itinerary: the Mad River Valley charming towns, Quechee Gorge, Sugar Bush Farm, and the Flume Gorge in Franconia Notch State Park.

States Nearby

  • I always check state borders too. If you are counting the 50 states, this easily gets New Hampshire, Massachusetts, and can swing into Connecticut and Rhode Island with an extra day. Don’t forget you are an hour from Canada in Stowe.
  • Last but not least, book the rental car, hotels, attractions, and dinner reservations. I’m coming for the apple cider donuts, fresh maple syrup, smoky cheeses, and maple creemee ice cream.
Woodstock has beautiful flowers for readers to love.
Woodstock

Vermont Road Trip Itinerary

This is a repeat of all the above information in a workable order for August. You will need twice the time for grid-locked October.

Day 1- Arrive in Stowe

  • Because of a $400 per-ticket price difference, we ended up flying into Boston instead of Burlington and driving 3.5 hours to Stowe.
  • 2-hour drive from Boston to Flume Visitor Center in New Hampshire.
  • Buy Flume Gorge tickets in advance. It is a 2-mile hike. There are more hiking options in Franconia Notch State Park.
  • Dinner at Chef Joe’s Catering, if you can find it in Franconia. Best food ever, but it’s mainly a locals’ spot.
  • Driving 2 hours to Stowe, you can choose two options: through Montpelier and Waterbury, or a more direct road that’s 20 minutes through more cute little mountain towns.
  • Visit Emily’s Covered Bridge that’s Haunted.
  • Alternative: Stay near Franconia, enjoy driving in the mountains, and visit the little towns tomorrow.
Waterfall in Franchonia State Park.
Flume Gorge Waterfall
The Flume Gorge is a top thing to do near Vermont.
Flume Gorge pond
The Flume Gorge is a top thing to do near Vermont.
Flume Gorge
Chef Joe's is about heavenly food and dinner with the locals.
Chef Joe’s
Readers want to see the chicken parmesan.
Chef Joe’s

Day 2- Stowe Itinerary

  • 8:30 to 9:30-Breakfast at Butler’s Pantry. If you want to head out earlier, grab Black Cap Coffee that opens at 7 am.
  • Smugglers Notch is the direction we are headed, with a few stops along the way. It is 11 miles and around 30 minutes.
The 200-year-old brick is neat for readers to see.
Butler’s Pantry

Bingham Falls

  • 10 a.m.- Our first stop is Bingham Falls Trail, 0.5 miles out and back. Allow an hour unless you plan to swim. Parking is VERY limited so arrive as early as possible. This is my favorite hike in Stowe.
  • There’s also Barnes Camp Boardwalk, an easy 1/8 of a mile boardwalk loop with views of the towering Notch Cliffs. It’s across from the gondola.
The waterfall cascades over rocks into a natural swimming pond for readers wanting to visit Bingham Falls.
Bingham Falls
The mountain views over the pond make it a great stop for Vermont travelers.
Barnes Camp Boardwalk

Mount Mansfield

  • 11 a.m.- The Mount Mansfield Gondola opens at 10 am for $50 per person at the Stowe Mountain Restort. The Cliff House is here for a lunch splurge (reservations recommended). You can hike up the mountain and ride the gondola down for free.

Auto Toll Road vs the Gondola

  • There’s also a 4.5 mile Auto-Toll Road up the mountain that’s almost equally expensive. It’s $40 a car and $15 a person in the car. If you have a van full of people, then drive the toll road. There’s a 1.5 mile out then back hike to the sweeping views. I’m not about tiny, dirt roads, going up and down a mountain and hiking when a gondola is nearby.

Summer View Debate

  • The BIG DEBATE: IS the gondola WORTH the MONEY in the summer? I understand $50 is a lot. Did I think the view was worth my money? I did. Is it overpriced? Absolutely! But I traveled here for this view. I didn’t find a cheaper comparable view elsewhere.
View of the mountains from the top of the mountain is the best of Stowe, Vermont. Readers want to see the gondola views.
Mount Mansfield

Smugglers Notch

  • 12 pm –Smugglers Notch is a winding, rocky road, with lots of rocks and a few hikes. I guess because I live in beautiful Alabama, I just wasn’t that impressed. I thought it would have a view of something, not just rocks.
Giant rocks are what make Smuggler's Notch unique.
Smuggler’s Notch

Sterling Pond

  • Sterling Pond Trail is steep and takes you to the highest trout pond in Vermont. It’s 2.3 miles out and back. Everyone says this is really hard and takes about 4.5 hours, so I can’t help you with this. This is located at the top of Smugglers Notch to the right of the parking lot.
  • You can rock climb with Sunrise Mountain Guides or Zip Line with ArborTrek Canopy Adventures.

The Von Trapp Lodge

  • 1 pm- The Von Trapp Lodge is famous for The Sound of Music family. With mountain views, Highland Cows, resort passes, and lunch options, give this place more time than an hour. This is the top place to stay in Stowe, and I didn’t allow enough time here to visit the grounds. The outdoor center, just down a bit from the lodge, sells the $15 resort ground passes.
The two-story lodge gives off a Swiss Apps feel.
Von Trapp Lodge

Highland Cows

  • Tours to meet the Highland Cows sell out weeks in advance, especially in spring with all the babies. The Kaffeehaus is an Austrian Bakery with the best apple pie and the cutest cow cakes. One of the pastures is behind the bakery, to see the cows.
  • It’s a great place for kids to ride bikes, hike, and spend a weekend.
  • The Brewery is the turn before the actual lodge for a quick meal.
  • The Main Dining Room serves dinner by reservation.
Baby cows and their herd of hairy, shaggy cows for readers of the Vermont Road Trip to visit.
Highland Cows
A little cake with cow horns and shaggy hair.
Cow Cakes
The brewery is a newer building without much history, just a place to eat.
Von Trapp Brewery

Stowe Bike Path

  • 3 pm-Rent bikes and ride the bike path in Stowe. The Path is 5.3 miles one way to the covered bridge, Brookdale, then back. This path is the definition of beauty and peace as it follows the river.
  • Due to a 70% chance of rain, we skipped renting a bike in advance at A.J.’s Ski & Sports or Mountain Ops for the Stowe Recreation Path. On weekends and peak season, rent in advance.
  • If you don’t have time for a ride, grab an ice cream at Red Barn and walk the path behind it for an hour after dinner.
The Stowe Recreation Path is a walk through the woods with a creek nearby.
Stowe Recreation Path
  • Dinner at Harrison’s at 6 pm – reservations 3 weeks in advance.
  • Then, we went for ice cream at the Red Barn and walked more of the Stowe Recreation Path behind the ice cream store.
  • Moss Glen Falls is 10 minutes outside of town and a 0.5-mile walk.
The pond and mountain views are just peaceful for readers of the Vermont Travel Guide.
Von Trapp Lodge View

Where to Stay in Stowe

  • The Von Trapp Lodge –It’s the best mountain views and natural setting.
  • The Stowe Village Inn – I wanted to be in town to walk around the shops (there are not many) and walk to dinner. I LOVED this historic house with a fabulous restaurant, river view, and live music. I would stay again.
  • The Lodge at Spruce Peak for skiing.
  • Vrbo- #3216804 or #4106621. The Stonybrook Homeowner’s Association is a residential condominium community set on 150 acres on the Stowe Recreation Bike Path. This means you can ride into town, with the most fun restaurant and the best Red Barn ice cream shop a walk away.
Stowe Village Inn is on the National Historic Places registry. The old farmhouse
Stowe Village Inn

Where to Eat in Stowe

Stowe has turned into a foodie town, with all 59 restaurants being above average.

  • Harrison’s- It wins lots of awards and is a hard reservation to land. The restaurant is small and in a basement. It has a romantic, expensive, speakeasy vibe and the food is top-level. However, for summer, I would have rather been at the fun restaurants with river views and live music. It’s downtown, and if you can’t get in for patio seating, try Plate. It’s basically next door.
Creamy ravioli to encourage readers to visit Stowe.
Harrison’s ravioli

Grant’s

  • Grant’s- It’s in the historic, upscale Stowe Village Inn with outside dining on a wrap-around veranda, live music, and delicious food. The home was built in 1814 and is on the National Register of Historic Places. It has a relaxed elegant vibe.
The live music makes for a vibrant atmosphere.
Grant’s

Idletyme Brewing

  • Idletyme Brewing Company– This place felt fun, with corn hole, flower gardens, and farm-to-table food. We found it while riding the Stowe bike path, so we stopped in. The Red Barn Ice Cream shop is nearby for a maple creemee.
The flowers, music, corn hole and fun vibe can be felt in this photo.
Idylltime

Doc Pond’s

  • Doc Pond’s- The restaurant plays over 1,000 vinyl records as background tunes. It is cozy and casual, with a no-reservations vibe. Burgers and fries are delicious.
  • The Bench- Serves woodfired pizzas and burgers reasonable priced in a cozy atmosphere.
  • The Butler’s Pantry– It’s the place to go for breakfast, located downtown in a historic building. They also serve seafood and steaks for dinner.
  • Cold Hollow Cider Mill – It’s only 10 minutes to grab a Dreamee apple cider with donuts in Waterbury.
The building shows readers where the fun starts,
Cold Hollow Cider Mill

Day 3 Burlington Itinerary

If you have to cut a day, this is it. Honestly, it just can’t stack up to Stowe and Woodstock for me, or I need more than a day. It’s an hour’s drive each way from Stowe, but we got stuck in road work, which doubled that. If you are flying into Burlington, here are a few things to do.

  • 10 am –Walk the Church Street Marketplace and Lake Champlain waterfront. Then we grabbed a great lunch at the Rogue Rabbit.

Shelburne Museum

  • 1pm -Head 10 minutes to Burlington for the Shelburne Museum for the Steamboat, circus, bridge, Dutton House, and Electra Havemeyer Webb Memorial Building for French art and Tiffany pieces, then Rail Car Isle. It’s basically a walk through time. We were here about 2.5 hours then headed back to Stowe for dinner. The Worlds Tallest Filing Cabinet is nearby at an intersection, so we circled by.
The historic daily products are neat to see.
General Store
Flowers grow abundantly in Vermont.
Gorgeous Flowers
Norman Rockwell is from Vermont, and his paintings are of everyday relatable life
Norman Rockwell
The wood and rock used to build this house make it unique.
Shelbourne Museum

Things to Do in Burlington

  • Have a Maple Creemee and ride the Burlington Bike Path.
  • Visit ECHO, an aquarium and science museum.
  • Take a lake cruise.
  • There’s also a Teddy Bear factory tour.
  • The Loch Ness Monster is said to have lived in Lake Champlain, so he lives on through the mascot for the Lake Monsters baseball team, 30-foot sculpture at ECHO, and a statue at St. Albans Bay Town Park.
  • I didn’t make it to the Champlain Islands for Grand Isle State Park or Knight Point State Park. There’s also Hackett’s Orchard and Allenholm Farm for cider donuts.

Visit Canada

Another Day Trip from Stowe is to visit Canada and the Haskell Free Library & Opera House that sits on the US & Canada border. Guided Tours are 45 minutes and $10, then visit Stanstead, Quebec.

Day 4- Woodstock Itinerary

Welcome to WOW! Woodstock delivers a movie-type perfect town. It’s a 2-hour drive from Stowe with hours of stopping at new places. If it’s leaf season, it might be an eight-hour gridlock drive.

  • Leave Stowe at 8-9 am headed to Woodstock.
  • Cold Hollow Cider Mill, which opens at 8 a.m. and closes at 6 pm, for apple cider donuts & an apple cider slushie with a maple creemee and donut. This is the most important stop for me today! We shopped and ate for an hour.
  • 10am- Stop in Ben & Jerry’s, which opens at 10 a.m., for the Flavor Graveyard or take a tour. I didn’t realize the tickets drop two weeks out and sell out.
  • Waterbury has a few restaurants, but it’s small.
  • Montpelier is the gold dome capital with streets filled with vintage stores. Morse Farm is nearby, also.

Sugarbush Farm

  • 12:30pm-Waitsfield has Sugarbush Farm for smoky cheese and watching maple syrup being harvested & the Great Eddy Covered Bridge. Y’all, just buy 2 packages of that smoky cheese. It travels for 4 days. Maple Butter too, if you have a cooler.
The age and wooden chapel set in the woods is unique.
Sugarbush Chapel
Snowfall markers are interesting to travelers reading the Vermont Travel Guide.
Snowfall for each year

Quechee Gorge

  • 1:30 pm- Quechee Gorge is 15 minutes outside of Woodstock, and you drive over it.
  • Simon Pearce for glassblowing, with a waterfall, covered bridge, restaurant, and the movie Sweet Home Alabama.
  • Taftsville Covered Bridge is located beside Simon Pearce.
Learning how glass is made is interesting for all travelers on the Vermont Road Trip.
Simon Pearce glass maker

Billings Farm & Rockefeller National Park

  • 3 pm -Arrive in Woodstock –Billings Farm & Museum & Rockefeller National Park (should be moved to another day, and just walk around the town). Buy tour tickets for the homes in advance.
  • 5pm -Woodstock shopping
  • Dinner at Worthy Kitchen
  • Woodstock Scoops for a maple creemee with maple sprinkles
The massive homes are unique to these rich areas 200 years ago so travelers want to see the old mansions.
Woodstock

Things to do near Woodstock

  • Drive 15 minutes over to Norwich to grab a snack at King Arthur’s Baking Company.
  • If you are traveling with kids, Killington has adventure courses and a mountain coaster. It’s about 30 minutes outside Woodstock.
  • Plymouth Notch is nearby and home to Calvin Coolidge too.
  • Orvis at the Woodstock Inn & Resort has fly-fishing guides.
  • Hike Faulkner Trail, Ottaqueechee River Trail, Eshqua Bog Natural Area, or Mt. Peg. I’ll say it again: I find the northern hiking harder, so good luck.

Where to stay in Woodstock, VT

  • The Woodstock Inn & Resort is THE luxury place to stay downtown. The rooms start at $700 a night and climb, so I can only dream.
The historic building, the grounds, and the flowers all feel like luxury.
Woodstock Inn
  • The Village Inn is a gorgeous PINK house in the heart of town that also serves dinner.
The pink old Victoria is a great place to stay in Woodstock for readers of the Vermont Road Trip.
The Village Inn
  • The Vesper – It’s in the heart of town, good beds and affordable. JB says it’s the worst breakfast of his life, with the oatmeal tasting like old towels, so go to a breakfast café.
Readers like to see the brick accomadations.
The Vesper
  • The Shire is close to downtown, but it’s not cute. It’s affordable.

Where to Eat in Woodstock

Honestly, Woodstock has more shops than restaurants downtown. I’m still looking for the best places.

The cute cafe is a great place to grab coffee or breakfast.
Mont Vert Cafe
  • Mon Vert Café- It was an easy place to grab breakfast and lunch downtown.
  • The Farmer and the Bell- a popular bakery with pastries and donuts. The donuts are rated the second best in all of Vermont.
  • The Ranch Camp is just a few steps outside town, and it smelled delicious.
  • Sunset Farm Restaurant had a crowd and a nice place to eat outdoors.
  • Worthy Kitchen has the best burger of the year. We both loved our food, and it was affordable and packed with locals.
Cute bakery for readers to plan their morning donuts at.
Farmer and the Bell

Day 5- Woodstock to Boston (3 hours)

  • If you didn’t make it to the Gorge, walk more around Woodstock, or visit Norwich, you can start the day with these
  • There’s Off the Beaten Path to Grafton

Grafton

  • Grafton preserved its 19th-century look.
  • The Grafton Inn was opened in 1801 and hosted Ulysses S. Grant, Ralph Waldo Emerson, and Henry David Thoreau.
  • The Phelps Barn Pub is at the Inn, so order the Vermont Cheese Board with all the local cheeses.
  • Grafton Village Cheese is famous for artisan cheddar, with tastings from 9 a.m. to 2 p.m.
  • Grafton Trails and Outdoor Center has 1,200 acres for biking, hiking, and skiing. A walking path includes the Kidder Hill Covered Bridge. Leave time for a stroll down Main Street.

Vermont Road Trip Extenders

  • You can stop in Hanover, Concord, or Manchester.
  • Salem is another option. The Ultimate Boston & Salem Travel Guide explores the history of the Revolutionary War, Fenway Park, the chilling town of Salem, and the Newport mansions on The Cliff Walk. Let’s meet in Boston in the fall.
  • I’m headed to Portsmouth for shopping and lunch at the River House since it’s my favorite. Then, on to the Hamptons for a day on Jenness State Beach. Mansions with a white powder sand beach- a perfect way to end my trip.

14 Day Road Trip Ideas

  • Extend the Trip to Springfield, MA, for the Dr. Seuss Museum and Old Sturbridge Village.
  • If you have more days, visit Mystic, Connecticut, or Newport, Rhode Island. Connecticut is America’s Hidden Gem, packed with living history towns, beaches, the oldest amusement park in the country, and waterfall hikes.
  • There’s always my personal favorite to turn this into a 10-day trip by driving down the coast of New England. 20 Things I learned on The Best Coastal Towns in Maine Road Trip including Acadia tips. Maine draws you in with the salty air, fresh lobster, boat filled harbors and towns with their own rhythm.

Savoring Vermont

Readers travel to see the mountains and ride a gondola.
Stowe

You can come for the famous fall foliage, but there is so much more to love beyond the leaves. A Vermont road trip is about the journey- the scenic drives, the waterfalls, historic homes, mountain views, and covered bridges. Maybe it’s the maple creemees, apple cider donuts, and smoked cheese and syrup that somehow make everything taste better. Whatever it is, Vermont gets under your skin. It isn’t a place you visit once. Vermont is a place you savor.

Thanks for reading my Vermont Road Trip Travel Guide. If you are looking for another fun road trip, check out Michigan. Michigan has beach towns that rival the Caribbean, the fairytale island of Mackinac, the rock formations on Lake Superior, and The Henry Ford Museum. This 10-day Michigan Road Trip begins in Detroit, winds through Wisconsin, and ends in Minnesota.

Empire's beach in Michigan is beautiful,
Empire

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Published on:
September 8, 2026
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Categories: Road Trips, UncategorizedTags: Route 100 Vermont, Stowe travel, Stowe Vermont Itinerary, Things to do in Stowe, Top things to do in Vermont, Vermont Itinerary, Vermont Road Trip, Vermont Travel, Vermont Travel Guide, Woodstock Vermont Itinerary

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