The Perfect Vermont Road Trip Itinerary + Insider Tips

Planning a dream vacation in Vermont and wondering where to go? This Vermont road trip itinerary takes you to the best getaways in Vermont

Vermont is a fun state, and a road trip is the best way to experience it. The Vermont road trip itinerary will allow you to see the best parts of the state in 5 days, but longer is recommended if you want to see even more.

I split this Vermont itinerary into five action-packed days, but you could always expand it to have more time in each place. If you prefer slow travel or want to do activities in each town that aren’t on the itinerary, expand each day below into at least two days, for ten or more days exploring this beautiful state.

I’ve packed this Vermont road trip with insider tips that will help you to make your experience as memorable as mine. Here you will find the best towns/cities to include and the top sites to see in each one.

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Vermont road trip

Essential Tips for Your Vermont Road Trip

Before you jump to the best things to do in Vermont, let’s talk about trip planning in Vermont and make sure you are prepared for the best experience.

I highly recommend coming to Vermont with a well-defined itinerary of the top things you want to see, visit and do, in order to maximize your time here.

Make sure you choose accommodation in a good area, where you can easily drive around and explore the main attractions. You can book a cozy cabin in Vermont or you can stay at one of the most beautiful boutique hotels in Vermont.

Lastly, if you need to rent a car for your Vermont road trip, you can get a 15% off your rental car when you book through this site. I use and recommend RentalCar because it is the most reliable rental car source, and it allows you to compare the prices of different places.

DAY ACTIVITYOVERNIGHT LOCATION
DAY 1: Explore Brattleboro, stop at the Creamery Covered Bridge, and visit the Grafton VillageWoodstock
DAY 2: Spend the day exploring Woodstock and visiting covered bridgesWoodstock
DAY 3: Drive the amazing Mad River Valley, visit Waitsfield and Warren Historic Center Warren
DAY 4: Explore Stowe, visit Ben & Jerry’s ice cream factoryStowe
DAY 5: Enjoy your day in Burlington, take a day trip to Shelburne Burlington
DAY 6: Visit the Hildene House, explore the Mount EquinoxManchester

5 Day Vermont Road Trip

DAY 1 Vermont Itinerary: Explore Brattleboro and Overnight in Woodstock

Ready to start your epic Vermont road trip? The first stop is Brattleboro in the southeast corner of VT. Throughout the day, you’ll make your way north to Woodstock, with many fun stops along the way.


1. Explore Brattleboro

Brattleboro sits on the Connecticut River in New Hampshire and is just ten miles north of the Massachusetts border. From the town, there are great views of the river and lots of restaurants. You can also make stops at the Brattleboro Museum & Art Center or the Vermont Center for Photography.

Vermont road trip

2. Creamery Covered Bridge & Bakery across the street

Less than five minutes west of Brattleboro is the Creamery Covered Bridge. The pedestrian bridge is the only one left in Brattleboro, and it’s over a century and a half old. Make sure you stop at The Vermont Country Deli across the way from the bridge for a tasty pastry or sandwich or to stock up on snacks for the rest of your road trip.

Vermont road trip

3. Grafton Village Cheese Company

Next on your Vermont road trip is to visit the Grafton Village Cheese Company, which is home to some of the state’s best cheese. All the cheese at the store is handmade in Vermont, using milk from the state. You’ll find cheese, wine, gifts, and more at the store. You can also sample cheeses at the store.

Vermont road trip

4. Saxtons River Distillery

Just over two miles north of Brattleboro is Saxtons River Distillery. The distillery makes small-batch spirits, many of which are maple based. They produce liqueur, bourbon, gin, and more, all of which are available to try at the distillery. Make sure you have a designated driver if you plan on drinking spirits at the distillery, especially since you have to drive to Woodstock, where you are staying for the night.


5. Spend the Night in Woodstock

Once you are done exploring Brattleboro and enjoying all the fun things to do there, it’s time to head to Woodstock, where you will be staying for the next two nights. Your drive is not too long, with just over 60 miles between Brattleboro and Woodstock.

Vermont itinerary

DAY 2 Vermont Itinerary: Explore Woodstock

Ready for another day of fun? On Day 2 of your Vermont road trip itinerary, you’re staying in Woodstock, where you can enjoy the town, your resort, or the outdoors with lots of fun wintertime activities if you visit during the season.


1. Explore Woodstock Downtown

Woodstock is considered one of the most beautiful cities in America for a reason. And it won’t disappoint you!

Start by taking a stroll down Main Street in Woodstock, and just get lost admiring the stunning array of buildings of 18th and 19th-century architectural styles. The best streets to mark on your map are The Green, Central Street, and Elm Street to get mesmerized by the beauty of Woodstock.

One of the most classic and beautiful buildings in Woodstock are the Norman Williams Public Library and the Woodstock Inn.

Vermont itinerary

2. Middle-Covered Bridge

Middle Covered Bridge is right across the street from the inn, so it’s the perfect way to start your second day of the Vermont itinerary. The bridge is one of the newer ones, built-in 1969. It was rebuilt after a fire and is open for vehicles and pedestrians.

If you love covered bridges, check out this list of the 20 best-covered bridges in Vermont.


3. Taftsville Covered Bridge

Next on your Vermont itinerary is the Taftsville Covered Bridge, as you won’t want to miss this beautiful site. The bridge is vibrant red and quite long, spanning over the Ottauquechee River. You will have to drive over to this bridge, which is three and a half miles east on US Route 4 from downtown Woodstock.

Vermont itinerary

4. Quechee Gorge

If you continue east from Taftsville Covered Bridge, you’ll reach Quechee Gorge. The gorge is great for a day of hiking, and there are a lot of trails, some of which take you to the bottom of the gorge. The park is beautiful in the fall when all the colorful foliage is blooming, and if you visit when the weather is nice, you can camp at the park.

PRO-TIP: While you are visiting the Quechee village, I recommend stopping for lunch at The Mill, voted one of American’s Most Romantic Restaurants. The food is amazing, cooked with local fresh ingredients, with very creative cuisine, and a stunning backdrop of the Ottauquechee River waterfall and covered bridge. If you are having dinner here I recommend making reservations in advance.

Vermont road trip itinerary

4. Lincoln Inn and Restaurant at the Covered Bridge

The third covered bridge near Woodstock is the Lincoln Covered Bridge. This bridge is in the opposite direction of Woodstock from the Taftsville Covered Bridge. It is just over three miles west on US Route 4.

Next to the bridge is the Lincoln Inn & Restaurant at the Covered Bridge. If the Woodstock Inn & Resort is booked, the inn here is a great alternative for where to stay during your time in Woodstock.


5. Woodstock Nordic Center / Suicide Six Ski Area (Wintertime Itinerary)

I highly recommend the Woodstock Inn & Resort during your nights in Woodstock. It is in downtown Woodstock, and you can walk to some of the places you’ll be visiting today from the inn.

Part of the Woodstock Inn is the Woodstock Nordic Center. You’ll find nearly 28 miles of skating and cross-country skiing trails just south of the main resort. At the center, you can rent snowshoes, fat bikes, winter clothes, and skis to use at the resort.

Another option for outdoor winter activities is the Suicide Six Ski Area, also called the Saskadena Six. The area is north of Woodstock, and you can take one of three ski lifts up the mountain and come down on one of the 24 trails.

PRO-TIP: Don’t forget to check the sky conditions to find out the best ski areas.

Vermont road trip itinerary

6. Ice Skating at Union Arena

Another fun winter activity in Woodstock is ice skating at Union Arena. The arena is just west of downtown Woodstock. You can ice skate here during public skate hours, and they have ice skates available to rent.

Vermont road trip itinerary

DAY 3 Vermont Itinerary: Explore Mad River Valley – Waitsfield/Warren

I hope you had a fun day in Woodstock, but now it’s time to head further north and explore the Mad River Valley. Today you’ll see more covered bridges and two small towns before heading to Stowe for the night. 

Best Accommodations: 1824 House Inn + Barn is a perfect accommodation located in Waitsfield offering many things to do such as hiking, cycling and golf. Or I recommend the Mad River Lodge also located in Waitsfield offering very comfortable accommodation.
Must Read: 10 Best Vacation Gateway in Vermont


1. Go on the 7 Covered Bridges Loop

As you already know, after day 2, Vermont has some amazing, covered bridges. Today, explore even more of them during a drive around the 7 Covered Bridges Loop.

The loop is 40 miles roundtrip, and if you spend time enjoying each bridge, it should take about half a day or so. Learn more about the Covered Bridge Loop.

During your stops at the Waitsfield Covered Bridge and the Warren Covered Bridge, stay to explore the towns and see the other sites today.


2. Waitsfield Historic Center

The Waitsfield Historic Center makes up the small town of Waitsfield. It was established in the early 19th century as a commercial hub for the farmers in the area. Be sure to stop by the Waitsfield Historical Society to explore the town’s history and get more information about events in Mad River Valley.

Waitsfield is also a great place to stop and shop, which is fitting since it was originally built as a commercial town. There are a variety of shops, including craft stores, art galleries, boutiques, a bookstore, and gift shops.

Vermont road trip itinerary

3. Warren Historic District/Warren General Store

The other place you have to stop along the Covered Bridge Loop is the Warren Historic District. The Warren Covered Bridge is in the historic town, as are many old buildings built in the 1800s. The town is on the National Register of Historic Places since it was an important mill town thanks to its location on the Mad River.

In the historic district is the Warren General Store. The store has a deli and a bakery where you can get fresh food and treats. They also have a big selection of craft beer, wine, fashion, and unique toys and gifts.


4. Warren Waterfall

South of the Warren Covered Bridge is Warren Falls. The waterfall flows into a natural swimming hole. Bring your swimsuit and jump off the cliffs around the hole if you visit in the summer.


DAY 4 Vermont Itinerary: Explore Stowe and Waterbury / Overnight in Stowe

After exploring Mad River Valley, you’ll spend a night or two in Stowe, VT. Stowe is one of the most popular places in Vermont, thanks to its famous ice cream factory and tall mountain and ski resort.

Best Accommodations: 1860 House Inn is set in a historic building and offers an old-style charm! The property is situated close to the center of Stowe village too so there are plenty of restaurants and shopping opportunities nearby.
Must Read: Best things to do in Stowe + Complete city guide


1. Explore Stowe Downtown

Stowe’s covered bridge is the Gold Brook Covered Bridge. The bridge is haunted by a girl named Emily, who died at the bridge, which is why it is also sometimes called Emily’s Bridge.

From the bridge, head into town and visit Stowe Church, one of the most picturesque churches in the state, with a beautiful mountain view behind it.

winter vacation in Vermont

2. Take the Cable car to Mount Mansfield

Even if you are not staying at the resort, you should take the cable car up the mountain. The views are amazing from the gondola, which runs in the summer. At the top of the mountain, the highest in the state, are hiking trails and a restaurant.


3. Visit the Classic Trapp Family Lodge

The Trapp Family Lodge is a historic lodge between the mountain resort and downtown Stowe. The lodge is close to the ski slopes and has an indoor pool, a hot tub, tennis courts, outdoor trails, and on-site dining.

PRO-TIP: One of the best accommodations options is the famous Trapp Family Lodge: This is one of the main attractions in Stowe and for a reason.


4. Ben & Jerry’s Factory

Finally, no matter how long you spend in Vermont, one of the places you cannot miss is the Ben & Jerry’s Factory. The factory is in Waterbury and is the only one open for the public to see. You can tour the factory and try the classic and newest ice cream flavors.

It makes a great short drive to visit the factory and try some of the amazing flavors, visit the gift shop and have some fun visiting the flavor graveyard where you can find all the retired flavors over the years.


DAY 5 Vermont Itinerary: Burlington and Shelburne

Day 5 of your Vermont road trip itinerary will allow you to spend the day in the small towns of Burlington and Shelburne, which are right next to each other. 

If you have more than five days in Vermont, I highly recommend spending a few more days in Burlington. You can slow down and spend more time at each of these sites.

Best Accommodations:  Williston Village In is in a great location and offers an escape from the hustle and bustle of everyday life. It’s also half the price of some of the other hotel chains in the area.
Must Read: Best Things to do in Burlington + Complete City Guide


1. Church Street Marketplace

Church Street is one of the main streets in downtown Burlington. The Marketplace, an outdoor mall, is one of the main attractions.

The marketplace has places to shop, eat, and entertain. The surrounding blocks have even more places, so you could spend a good part of your day here.


2. College Street

College Street is one of the other main streets in Burlington which runs perpendicular to Church Street. The street has great restaurants and coffee shops. It runs west to Lake Champlain, so it’s a good street to walk down if you are heading to the lake.


3. Visit the Shelburne Museum

The final stop today is in Shelburne, just south of Burlington. The Shelburne Museum is home to over 100,000 pieces of folk art. The museum spans multiple buildings and on the site is a toy shop, multiple art galleries, and a covered bridge.

winter in Vermont

4. Lake Champlain

Burlington sits on Lake Champlain. You can enjoy the lake from the Waterfront Park or at one of the many lake-side restaurants. Or, you can rent a boat or a kayak and see Burlington from the water.


DAY 6 Vermont Itinerary: Manchester

The final day of your Vermont road trip itinerary is going to be a lot of fun! It’s time to head back down south to Manchester in Southwest Vermont. The drive from Burlington to Manchester is 100 miles and by the end of the day, you’ll have looped around the whole state in less than a week.

Best Accommodations: The Inn at Manchester is set on four acres of landscaped gardens so there’s plenty of room to explore. You’ll also be close to Manchester town center which has lots of charming restaurants and shopping opportunities.
Must Read: 18 Awesome Things to do in Vermont in Winter


1. Hildene House

Start the last day of your Vermont itinerary by visiting the Hildene House the home to Robert Lincoln, son of President Abraham Lincoln. The home sits on 412 acres and has tours, educational exhibits, and hiking trails.

There are also seasonal events like Christmas decor in the winter and peony season from late May to June in the gardens. On the home’s farm, there are animals to visit and a cheesemaking area.


2. Mount Equinox

Your final stop, and one of the prettiest, is Mount Equinox Skyline Drive. The paved road takes you through 5.2 miles of mountains up to the top of Mount Equinox. Along the drive, there are many lookouts and picnic areas to stop at and enjoy the views.

Then, at the top, you’ll get the best views from the 3,848-foot summit where there are picnic areas and a visitors center to end your day.

PRO-TIP: The drive is open from Memorial Day weekend through October. Make sure to visit when the weather is clear so you can see all the mountain views.

things to do in Vermont in winter

Vermont Road Trip | Trip Resources

Planning a Road Trip in Vermont

If you are going on a road trip to Vermont, pre-planning, researching, and understanding what you are looking for in a destination will help make your travels far more successful and safe.

Here is some further information I think you might need to plan your Vermont itinerary. Make sure you check the following too:

15 Incredible Cabins you can Rent in Vermont
15 Best inns & boutique hotels in Vermont
Winter Vacation in Vermont: 10 Perfect Winter Getaways!
13 Awesome Things to do in Stowe in winter
15 Terrific Things to do in Burlington in winter
20 Amazing Things to do in Woodstock, VT
18 Awesome Things to do in Vermont in Winter

Best Accommodations in Vermont

When planning your Vermont Road Trip, make sure you choose accommodation in a good area, where you can easily drive around and explore the main attractions.

Making your reservations in advance is also part of a well-planned visit, as depending on what time of the year you are visiting Vermont it may be hard to find last-minute accommodations.

For an even more authentic experience, consider booking a cozy cabin in Vermont or you can stay at one of the most beautiful boutique hotels in Vermont.

Booking.com
13 things to do in Stowe VT in winter

Driving tips for your Vermont road trip

If you are taking a road trip during winter time, a 4×4 car is not necessary, but it is nice to have if you are planning to drive outside the town.

Lastly, if you need to rent a car for your Vermont road trip, you can get a 15% off your rental car when you book through this site. I use and recommend RentalCar because it is the most reliable rental car source, and it allows you to compare the prices of different places.

What is the Best Time To Visit Vermont?

FALL: It is the most popular time of the year to visit Woodstock because it is when the fall foliage changes from early October to around the third week of the month. It is important to plan in advance, especially make your accommodations in Vermont well in advance. Prices for hotels and flights will be the most expensive during these months.

WINTER: The fact is that the whole state of Vermont is cold in winter – with temperatures that can drop below zero. But as long as you pack accordingly, you will love it because the snow makes Vermont’s landscape look and feel even more spectacular! Make sure to check the weather, and have fun on the snow slopes around Woodstock!

SUMMER: During summer time Woodstock offers great outdoor eateries, swimming holes, and a great brewery to enjoy the outdoors. The warmest time of year is generally mid-July where highs are regularly around 84.9°F (29.4°C) with temperatures rarely dropping below 59.5°F (15.3°C) at night.

SPRING: Spring is a beautiful time to visit Woodstock, plus it is a perfect time to visit for a quiet and peaceful getaway. There are many things to do outdoors that will allow you to enjoy, such as the maple syrup flowing, enjoying the spring wildflowers, and drinking a local beer seating outside around a fire pit.

What to Pack for your Vermont Road Trip?

Make sure you are prepared, considering the season and the activities you are planning to do. Here are some quick tips:

  • Pack layers of clothes so you can be comfortable in the changing temperatures!
  • Bring a pair of jeans and a light sweater to wear in the evenings
  • Pack rain gear – you don’t want to get soaking wet while exploring
  • A hat, gloves, and scarf can’t go wrong, even in summer.
  • If visiting in winter, bring good quality sturdy snow boots.
  • Bring warm leggings to wear as a layer is a smart choice!
  • Pack a good jacket, check my complete review guide on the Top Jackets for Travel
  • If you are planning to carry a backpack for your trip to Vermont, I have compiled a very detailed review of the Best Backpacks for Travel on the market today

PACK SMART ALERT!

If you are planning to carry a backpack for your trip to Alaska, I have compiled a very detailed review of the Best Backpacks for Travel in the market today – Also, I recommend bringing a good and warm jacket waterproof jacket for your trip, check my complete review guide on the Top Jackets for Travel Bring some warm pants, you can check the best Warm leggings in the market – especially because they are a great option for layers too.

Vermont Road Trip Conclusion

I hope you have enjoyed this Vermont road trip itinerary!

Vermont is a fun state, and a road trip is the best way to experience it. A 5-day road trip will allow you to see the best parts, but even longer is recommended if you want to see and do more, such as visit all the 10 best gateways in Vermont.

This Vermont itinerary includes the bigger cities of Montpelier, the state capital, and Manchester, but also, will take you to the best towns while experiencing covered bridges, and amazing farm-to-table fresh food.

If you have any questions, leave a comment below and I will be happy to help!

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Road trip in Vermont

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