The Ultimate Guide to Vermont Fall Fun: What You Don’t Want to Miss!


Each September, when school starts again and subtle hints of fall creep into the air, I get the itch to start filling my weekends with our absolutely glorious Vermont fall activities.

Come on… Vermont fall is incredible, and it offers countless options for seasonal enjoyment. To help you out, Vermont Mom compiled the Ultimate Guide to Vermont Fall Fun to help you and your family enjoy the season in our beautiful state! Below, you’ll find all the best spots for leaf-peeping in Vermont, the best places to stop for eats along the way, a variety of festivities happening around the state, and other locations where you can participate in some fall fun!

And please… while we do our very best to stay up-to-date with events, it’s always a great idea to check and make sure the Vermont fall fun activity or event is still happening.

Delicious Autumn Panoramic

Mount Philo and Vermont Cookie Love

Enjoy western views overlooking Lake Champlain and beyond from the top of Mount Philo. The perfect excursion for all abilities and generations, you can choose to hike the trail, walk the road, or drive on up to the summit. Bring a picnic, then stop at Vermont Cookie Love in Ferrisburgh on your way back home for freshly baked fall-tastic cookie flavors like oatmeal, coconut, chocolate chip, dried cranberry, almond (that’s all one cookie!) or pumpkin chocolate chip.

Be a Tourist in Your Own State

Stowe Gondola SkyRide and Cold Hollow Cider Mill

You’ll find both the Stowe Gondola SkyRide and Cold Hollow Cider Mill on many tourist must-do lists, for good reason. The views that emerge as you ascend Mount Mansfield on the gondola wow any and all foliage enthusiasts and kids will love the gradual, smooth ride. Once up top, choose to hike around or just rest and take it all in. On your way out of town, grab a dozen piping hot cider donuts from Cold Hollow, voted best cider donuts by Seven Days readers.

Fall Road Colors
Colorful Vermont roads in fall.

Colors on the Move

Fall Foliage Train Rides and King Arthur Bakery + Café

Leaf peeping doesn’t have to take place from the top of a mountain ridge. On the contrary, Vermont’s towns and valleys are as spectacular as the mountains during foliage season. Take in the beauty of hillsides, rivers, and covered bridges surrounded by autumn colors on a Fall Foliage Train Ride, departing from Chester, Vermont. Round trip train rides to Ludlow, VT are offered once per day and last two hours. A shorter, one-hour, round trip train ride to Rockingham is also available twice per day on the same dates. On your way to Chester, take a slight detour to the King Arthur Flour Bakery + Café in Norwich. King Arthur Flour rules seasonal baking, virtually guaranteeing fall goodies right when you want them.

Fall Immersion

Little River History Hike and Prohibition Pig

Seeing the autumn colors is one thing. Being inside the colors is a whole other experience. Through Columbus Day weekend, Little River State Park is an ideal spot to immerse yourself in the fall scenery. The History Hike is much more a walking journey back in time than a hike. The trail meanders through beautiful forest, past stone walls, foundations, and orchards from a century ago. You may work up an appetite, so head into Waterbury for lunch or dinner at Prohibition Pig. While known for classic cocktails and craft beer (not that there’s anything wrong with that!), kids and adults alike will love the hearty BBQ comfort food.

Vermont Fall Treats
The flavors of fall abound in Vermont.

Profile-Worthy Photo Op

Moss Glen Falls and The Warren Store

Route 100 through the Mad River Valley follows the eastern edge of the northern half of the Green Mountain National Forest, making it one of Vermont’s most scenic stretches of road. Tucked into the forest in Granville you’ll find family-favorite Moss Glen Falls, a breathtaking waterfall just a short walk into the woods, with easy access from Route 100. A backdrop of fall colors makes the waterfall even more sensational. On your way to or from the falls, round off your quintessential Vermont experience at The Warren Store. Order a sandwich on homemade bread at the deli or a whoopie pie from the bakery in the barn out back.

When Should You Go?

Pinning down peak foliage is tricky. Luckily, there are plenty of others doing it for us. Check the Vermont Travel & Tourism Foliage Forecaster or the Yankee Live Foliage Map to plan your optimal trip. Then get out there with your favorite people and soak in the autumn beauty, because pretty soon you’ll be giving it up for the frosty Vermont winter.

Fall Colors Reflected in Water
Vermont’s forests, fields, and mountains are at their best in fall.

Vermont Fall Fun Festivals and Events

1. Harvest Festival at Shelburne Farms


Cost: $10 adult/$5 seniors and children/children 2 years and under are free/admission is free for membership holders 

This annual festival never disappoints! The barnyard animals will be out for visiting as always, but this festival offers so much more! Join this fall celebration and enjoy a variety of live music and other performances, fresh farm food, local artisans, and a plethora of free activities for kids. In the past, they have offered horse-drawn hayrides, as well as live bird presentations.

2. Colors of the Kingdom Festival, St. Johnsbury

September 18, 2021, 8am-5pm

Head to downtown St. Johnsbury and celebrate fall with free or low-cost events, including “train rides, a farmers market, arts & crafts fair, planetarium shows, bluegrass musical festival, a parade, and much more”!

3. Shoreham Apple Fest, Shoreham

September 19, 2021

The Orchard Run at Applefest kicks off this event at 10:30 on School Road. Then, beginning at noon, the town green will be abuzz with farmer’s market booths and a pie contest. Drink samples, including both hard and sweet ciders, will also be available. An annual fundraising event for the Platt Memorial Library, attendees’ lunch purchases will benefit this worthy cause. This year, the library is planning on selling pulled pork sandwiches with coleslaw, baked beans, and apple desserts. Yum!

4. Bristol Harvest Festival

September 25, 2021, 10am-4pm

At this festival, you’ll find no shortage of craft and vendor booths, food, live entertainment, and other activities.

5. Sam Mazza’s Harvest Weekends, Corn Maze, Hayrides, and Annual Pumpkin Weigh-In, Colchester


Sam Mazza’s Fall Harvest Weekends are a great family fun option. Every week, their delicious Apple Cider Donuts and Apple Pies will be available and each weekend will feature different activities, as well as food vendors.

From Labor Day Weekend – October 31st, Monday-Saturday 10 am-6 pm, Sunday 10-5, Sam Mazza’s Corn Maze will be open. Note that no maze tickets are sold within an hour of closing.

On September 19, 10 am-4 pm, Mazza’s will hold their Annual Giant Pumpkin Weigh-In

Hayrides to the pumpkin patch: DATES UNKNOWN. 

6. Old Fashioned Harvest Market, Underhill

September 25 & 26th, 2021

This year’s annual Old Fashioned Harvest Market kicks off with a parade at 9am.

The festival is full of fun activities for the kiddos, over 100 craft vendors, a dog parade, and live entertainment including music, delicious food options, hayrides, and more. This two-day extravaganza has it all!

7. Stowe Foliage Arts Festival

October 8 – 10, 2021, Festivities start at 10 am each day

This festival occurs during peak foliage season and features over 150 fine artists and artisans, live music and a variety of other entertainment, and delicious food!

8. Harvest Weekend Billings Farm and Museum, Woodstock

October 9 & 10, 2021, 10- 5pm

An admission fee is charged*

This party includes a traditional corn husking competition and also includes a barn dance! Kids and adults can learn how to press cider and harvest root veggies. Don’t forget to find some donuts and hot spiced cider as well! This museum is a must-visit for families — the foliage on your way to Woodstock is a fantastic bonus! And check out their full schedule of events too! 

9. Montpelier Fall Festival, Montpelier High School

October 31, 2021, 10am-2pm

This event supports the local schools of Montpelier. Festivities include crafts, food, and games. You can sign up for their popular one-mile fun run here! And… we have three words for you: THRILLER FLASH MOB.

10. East Charlotte Tractor Parade

October 11, 2021

Ever see a parade of 200 tractors? Well, here’s your chance! This Vermont favorite also features a variety of vendors selling crafts, food, clothing, and so much more! Parking is available in the field off of Sheehan Green Development, which will be well marked with signs! Festivities begin at 10 am at Nichol’s Farm, heading towards Spear Street.

11. Isham Family Farm 

September 25, 26. October 3, 10, 16, 17, 23, and 24, 2021

This lovely family farm hosts a variety of fall activities and smaller harvest fests during many weekends. You should confirm times and dates on their Facebook page.

man, girl, apple treeApple Picking Corner

Fall without apple picking is like summer without creemees. We have so many wonderful orchards to choose from and enough weekends to hit up several, if not all of them! After all, not every variety is available at the same time, and you’ve got to balance out your Macintoshes and your Red Delicious. Fill your baskets and test out different pie recipes, make an epic vat of homemade apple sauce, or just eat the crunchiest ones straight up. The doughnuts aren’t bad either. Check out this list to work out your pickin’ schedule!

Adam’s Apple Orchard & Farm Market, Williston

Boyer’s Orchard and Cider Mill, Monkton

Chapin Orchard, Essex Junction

Hackett’s Orchard, South Hero

Hall’s Orchard, Isle La Motte

Happy Valley Orchard, Middlebury

Shelburne Orchards, Shelburne

sign, corn maze, enter

Corn Maze Frenzy

Lose yourself in a dizzying farm labyrinth or a “maize maze,” if you will. Your kids will love running around the puzzle trying to find their way out. Here are some fun ones to visit!

1. Great Vermont Corn Maze, North Danville

Well worth the (amazing foliage) drive to the Northeast Kingdom, this Top-10-in-America rated option is the ultimate corn maze experience. Seriously, this thing is huge. The website recommends starting before 1pm.

2. Isham Family Farm, Williston

This maze is made out of both corn and sunflowers! As you search for the exit sign, you’ll also be playing scavenger hunt. Good times!

3. Percy Farm Corn Maze, Stowe

Enjoy a scenic drive to one of the most charming towns in Vermont, Stowe! Work up an appetite solving the maze, then head to one of the town’s adorable restaurants for lunch or an early dinner. Bonus: This maze is dog-friendly, but leashes are required for Rover.

4. Whitcomb’s Corn Maze, Williston

Last but not least, Whitcomb’s combines their maze with learning, as you reach checkpoints that teach you all about pumpkin harvesting! Perhaps you will also find the candy jackpot hidden within the 4-acre maze, or maybe the specially marked ear of corn that entitles you to a free small pumpkin. They open on September 18th for the 2021 season!

And speaking of pumpkins…

pumpkin patch

Pumpkin Picking

When we think October, we think pumpkins, and we’re not just talking about fancy coffee drinks here, but actual pumpkins! If you’ve never picked your own straight from the patch, you are missing out on some serious fall fun. Here are a few places to choose from as you hunt for the perfect jack-o-lantern candidate. Don’t forget to roast those seeds for a well-earned reward (because you know you’ll be doing most of the carving work, not the kids).

Chapin Orchard, Essex Junction

Isham Family Farm, Williston

Parker Family Farm, Williston

Red Barn Gardens, Williston

Sam Mazza’s Farm Market, Colchester

Shelburne Orchards, Shelburne

Whitcomb’s Land of Pumpkins, Williston

parent trick or treating with child

Halloween Hoopla

1. Trunk or Treat and Pumpkins in the Park, Milton


Now that you’ve picked the perfect pumpkins, it’s time to carve them- and what better way than somewhere that’s not your house? Bring the mess to Milton instead! They will even provide stencils, decorations, and carving tools. The event will also include costume and best carving contests with prizes, as well as trick or treating, refreshments, and a big bonfire.

2. Haunted Happenings, Shelburne Museum


Cost: Free with Museum Admission

Put on your costumes and head over to Shelburne for this incredible event that combines candy with culture — the best of both worlds! Named a Top 10 Fall Event by the Vermont Chamber of Commerce, this spooktacular fall fun shindig turns the museum into a trick-or-treating tour as workers dress up to hand out candy. Wrap up with lunch at the cafe, now featuring Skinny Pancake.

3. Halloween Family Party at University Mall, S. Burlington

Details for this annual event have not been posted yet. Please stay tuned to the University Mall Facebook page for details!

Knock out some early Christmas shopping while your kids are rewarded with candy from every store you drag them to. They can also enjoy fall fun activities, like a pirate train ride and a bouncy house!

4. Trick-or-Treat Street on Church Street, Burlington


Enjoy trick-or-treating, face painting, and other seasonal activities on our beautiful, car-free favorite downtown Burlington street.

5. Swim with the Pumpkins at Burlington YMCA


Registration is required on the YMCA website

Children can go pumpkin picking in the pool and take home an inflatable or real pumpkin. Light refreshments are also provided.

6. UVM Horse Barn’s annual Halloween Barn


Horses and owners dress up for Halloween! This fun and candy-filled excursion is great for horse-lovers of all ages.

7. Essex Trick or Treat Trail

October 30, 4-8 pm. Preregistration required- it is $5 per group.

This fun and spooky walkway ends in a giant wall of jack-o-lanterns. Check back to find registration info.

8. Catalyst Church Trunk or Treat, Jericho

October 31, 3 pm. Dress up for maximum fun!

Jack-o-lanterns spelling out "Winooski Strong"
Photo used with permission from Meredith Bay-Tyack

9. Halloween in Downtown Winooski

October 29 – 31, 2021

Free, open, and inclusive of all, Halloween in Winooski features music, activities, and crafts- and the beloved 1,000 jack-o-lantern display in Rotary Park, which is the ultimate photo opp for dressed-up kids and adults alike. The parking garage is free all weekend.

Above all, friends, remember to enjoy this festive harvest season!

Guide to Vermont Fall Fun


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