Things to do in Southern Vermont – Best Fall Itinerary

Southern Vermont has to be the most underrated region of Vermont in autumn. Southern Vermont is the only place in the state where you can go from the top of a mountain to a lake in less than 20 minutes, making this area of Vermont special because you can experience varied fall foliage by taking advantage of the different elevations.

In this post, we’re sharing a one-day itinerary to help you optimize your time in Southern Vermont. We include everything from the top activities to the best restaurants, hikes, accommodations, and more. With its proximity to the Green Mountains, it’s the perfect spot for someone looking to enjoy the outdoors and small-town charm of Vermont.

This post is put together in partnership with the Southern Vermont Deerfield Valley Tourism Board. All opinions are authentically our own.

Weekend in Southern Vermont Itinerary

Breakfast

Start your day with breakfast at Dot’s Restaurant. You can’t go wrong with Dot’s! The portions are generous, the service is quick, and people are friendly. Elliot ordered the Cajun Skillet, and I ordered the Veggie Omelet with cheese. Dot’s Restaurant was completely restored after flood damage caused by Hurricane Irene in 2011 and has a beloved local history. It’s the perfect way to begin your stay in Southern Vermont!

Two other great breakfast options in town are Mill & Whistle Café or Village Roost Cafe. Both are located right in Downtown Wilmington.

Hike or Paddle Harriman Reservoir

Next, it’s time to enjoy some time outdoors for a hike or paddle. There are several great hikes in the area, including the Haystack Mountain Trail or the Hoot Toot and Whistle Trail at Harriman Reservoir. We opted to rent kayaks from Equipe Sports in Dover (Mount Snow location) and kayak the Harriman Reservoir to take advantage of seeing fall foliage from the water. We met one of the Equipe Sports staff at this boat ramp to put in our kayaks.

While you can easily make this an all-day activity since the reservoir is large, we opted to explore the northern section of the reservoir, close to the Deerfield River. Since the river section was narrower, it put us in closer proximity to the fall foliage. If you choose to head south on the reservoir, there’s a great little island that would make a great midday picnic spot!

Keep in mind, if you do rent kayaks from Equipe Sports in Dover, they require you to sign documents at their office. We opted to have Equipe Sports deliver and pick up the kayaks to Harriman Reservoir. Incorporating kayaking into your plans would require you to be cautious of their drop-off and pick-up times. If you’re renting kayaks, you might want to enjoy them for the full time of your rental, making it an all day activity.

Lunch and Vermont Maple Creemees

After kayaking or hiking and working up an appetite, we recommend heading up Vermont Route 100 and getting lunch at Nomad Buns + Bowls. We ordered the Nomad Pork Bun and the Brisket Bao Bun, and they were both phenomenal! If we didn’t have our eyes on a Maple Creemee right after lunch, we would have also ordered one of their legendary Ramen bowls.

While you’re there, you can stop by River Valley Market to peruse their selection of locally made foods. They would be a great spot to pick up some locally made cheese, apple cider, or other deli items! We picked up some firewood for a campfire in the Green Mountains here.

Next, walk across the street to the Creemee Stand for a classic Vermont Maple Creemee. The Creemee Stand was rated one of the best maple creemees in Vermont and is a must-do while in Southern Vermont! If Southern Vermont is just one stop on your trip, be sure to pick up a Vermont Creemee Passport. Local businesses have a custom stamp you can use to track your maple creemee consumption in your Creemee Passport.

Scenic Ski Lift up Mount Snow

With full bellies, spend the afternoon enjoying the views from the top of the mountains at Mount Snow. We recommend riding the ski lift up to the top, where the sweeping views of the Deerfield Valley and Somerset Reservoir are sure to leave you breathless. The ski lift runs Friday through Sunday from 10 am to 5 pm.

You can either ride the ski lift up to the top or hike up and take the ski lift down for a reduced price. Mount Snow also makes a great spot for mountain biking! Visitors can take their designated mountain bike lift up the mountain and enjoy coasting down to the bottom.

Once you make it to the top, visit the Bullwheel, which is open from 11 am to 4 pm and offers drinks and a Mexican-inspired menu. Elliot enjoyed a beer, and I enjoyed a hot apple cider on the deck overlooking the Somerset Reservoir, and it was peak Vermont fall vibes! The views are incredible and give you both the mountains and the water in one view.

Dinner

For dinner, we recommend enjoying pizza and beer overlooking Vermont’s 100 Mile View at Beer Naked Brewery and Pizzapalooza! Beer Naked Brewery features locally grown hops from Hoppy Valley in Pownal, VT. They also use fresh and local ingredients that make their pizza stand out. We enjoyed a half Roni Up and a Fungi wood-fired pizza that really hit the spot after a full day exploring. Elliot ordered their IPA and I ordered their cider – both were delicious!

The thing that takes Beer Naked Brewery over the top is their location, which gives views 100 miles into the distance, so you can watch the sun set over the mountains. They also offer camping through HipCamp and are dog-friendly. We don’t think there’s anything better than ending our day with pizza and brews with some incredible views.

Although we didn’t get to visit, we received several recommendations for Snow Republic Brewery and Alpenglow Bistro! If you’re wanting a more low-key night, many of the Inns have a small restaurant at their locations that’s worth asking about.

Top Fall Things to do in Southern Vermont

Southern Vermont is the perfect destination for an authentic Vermont fall getaway! It has all of the classic fall activities and things to do without the big crowds in northern Vermont. Below, we’ve compiled the best fall activities in Southern Vermont:

Take a Scenic Drive

Southern Vermont has two great scenic drives, including Scenic Route 100 Byway and Molly Stark Byway. The Molly Stark Byway (State Route 9) is the main east-west route in Southern Vermont that connects Brattleboro, Wilmington, and Bennington. We recommend stopping at the Hogback Mountain Overlook (aka 100 Mile View) to take in the sweeping views!

Southern Vermont is also the perfect place to begin the Scenic Route 100 Byway. This road runs north-south through the state, connecting several idyllic towns.

Ride a Scenic Ski Lift

Head to Mount Snow and take the ski lift up to the top. Enjoy the scenic views of Mount Snow and the Deerfield Valley below, but make sure to stop by the Bullwheel for drinks and food, where you can sit outside on their deck overlooking the Somerset Reservoir below! It’s a top-notch fall experience!

Take a Fall Hike

Southern Vermont has several great hikes in the area for outdoor enthusiasts. You can hike the Haystack Mountain Trail, which is a 4.2-mile hike with just over 1,000 feet of elevation gain, or hike the Lye Brook Falls Trail, which is one of the most popular hikes in the Green Mountains National Forest and is 4.5 miles with about 900 feet of elevation gain, and takes you to a waterfall.

We opted to hike the Mount Olga Fire Tower in Molly Stark State Park, which has sweeping mountain views. There are two trails to get to the fire tower: the Mount Olga Trail in Molly Stark State Park or the Mount Olga via Tower Trail, which is what we did! The climb up the fire tower is not for the faint of heart, but it is definitely worth it if you’re not afraid of heights!

Enjoy Fall Treats

Apple Cider is a classic fall treat, and there are many places to enjoy it in Southern Vermont. We enjoyed it on the deck at the Bullwheel at the top of Mount Snow, overlooking the Somerset Reservoir. Alternatively, you could also pick up locally made apple cider from the Farmhouse Market, River Valley Market, or Hogback Mountain Country Store.

You can’t visit Vermont without trying Maple Creemees. We enjoyed our first Vermont Maple Creemee at the Creemee Stand and it lived up to the hype. We wish we had learned of the Vermont Creemee Passport earlier so we could have tracked our maple creemee consumption with the fun custom stamps.

Head to the Water

Get out on the water before it freezes for winter by going for a kayak paddle or on a SUP on the Harriman Reservoir or Somerset Reservoir. We opted to rent a kayak from Equipe Sports in Dover (Mount Snow location), and it really elevated our experience, being able to see the fall foliage from the water. It’s a relaxing and fun activity to take advantage of the water access this area of Southern Vermont has.

Shopping Local Businesses

Explore downtown Wilmington and its local shops! Vermont is known for its local, small businesses, and the ones in Southern Vermont do not disappoint! We recommend walking around downtown Wilmington, which is quintessential small-town Vermont to search for some locally made items.

We perused several stores, but our favorites were by far Arthouse Studio Gallery & Lounge for one-of-a-kind pieces made by local artists, the local independent bookstore, Bartleby’s Books, for Vermont authors, and Quaigh Designs for handmade apparel, pottery, and crafts. Wilmington also has a great used bookstore, West End Used Books, just further down the street if that’s more of your interest. We picked up some divine-smelling goat milk hand soap from Quaigh Designs and really enjoyed speaking with the store owner about her passion for quality handmade crafts.

Try the Local Restaurants

Southern Vermont has countless great restaurants that feature locally grown ingredients. While we were in town, we visited some local favorites, including Dots Restaurant, Nomad Buns + Bowls, and Beer Naked Brewery. There are several great restaurants that we didn’t get to try, but we’ll have to sample on a return trip to Southern Vermont.

How to Get to Southern Vermont

Southern Vermont is a great location for a weekend trip, to be added to a larger Vermont road trip, or a fun day trip.

• The largest, closest airport is the Boston Logan International Airport (BOS) in Boston, Massachusetts, and is a 2:30 drive away from Wilmington, Vermont.
• The closest airport, Albany International Airport (ALB), is a 1:30 drive away and takes you along the scenic Molly Stark Byway.
• Lastly, the Burlington International Airport (BVT) located in Burlington, Vermont, is 2:40 drive away and makes a great option if you’re planning a larger Vermont road trip.

Best Time to Visit Southern Vermont for Fall Colors

Generally speaking, the best time for fall colors is mid-September through early October. With that being said, peak foliage changes from year to year. Changes in temperature and wind can remove foliage in fall storms, and changes in recent rainfall are all factors that affect the fall colors and the duration of the fall foliage.

We highly recommend looking at the Southern Vermont Deerfield Valley Tourism Board website for the latest updates on fall foliage! They update it weekly, and it really helps to have a local’s perspective on where the foliage is.

(photo: foliage tracker)

Fall Festivals in Southern Vermont

When planning your travels, you may or may not want to attend some of the great festivals in the area. The Vermont Fall and Harvest Festival is in the middle of September each year in Wilmington and Dover. The Festival spans three days, moving attendees through picturesque Deerfield Valley for wine tastings, farm-to-table dining experiences, shopping, hiking, and more.

Mount Snow Oktoberfest is held on the first and second Saturdays in October each year. It includes a keg-throwing competition, a stein-holding competition, and yodeling. If you enjoy Oktoberfest in full festival mode, we would definitely check out Mount Snow’s!

Tips for Visiting Southern Vermont in the Fall

After visiting Southern Vermont in the fall, we learned a few things that we’d recommend for having the best time!

1. Bring Cash – some restaurants and businesses don’t take credit cards, so be prepared with cash.
2. Wear Layers – The fall weather can be fickle, so be sure to wear layers. You can start the morning on the lake at a lower elevation and then end the day at a mountaintop where it can be much cooler. Also, bring a rain jacket for potential rain. We got caught running back to our van in the rain because we didn’t bring our rain jackets on a hike.
3. Check the Foliage Tracker – The Southern Vermont Deerfield Valley’s foliage tracker is updated weekly, so this helps to keep your expectations in check depending upon where you’re traveling from.

Where to Stay

Southern Vermont has tons of great accommodations! Since we traveled with our van, we opted for some of the many camping options. We’ve also included a list of some of the cute Bed-and-breakfasts, Inns, and unique accommodations!

Camping in Southern Vermont

Southern Vermont has a ton of camping options! Whether you’re interested in staying in campgrounds with full amenities or boondocking on public lands for free, Southern Vermont has it all!

Our favorite place we stayed in Southern Vermont was in the Green Mountains National Forest. We stayed at the Somerset Airfield Campground for a few nights and really enjoyed it. The Somerset Reservoir is located 3 miles up the road and is another great spot for getting out on the water with a kayak or SUPs. At the time of our visit, it was free, but that might change in the future. There were pit toilets and designated camping spots with rock fire rings.

Just north of the Somerset Reservoir is the Grout Pond Recreation Area, which has designated campsites with firepits and picnic tables. They are $16 per night, or less with the Senior America the Beautiful passes. Some sites even overlook the water!

As for private campgrounds, we stayed at the Greenwood Lodge & Campsites campground for one night to recharge our batteries and really enjoyed our stay! The family-owned campground had several sites, many of them with trees to give privacy between the sites. Although the showers were a little small, they were super clean, and the family running the campground was incredibly kind and helpful. The property had several trails to walk our dog, which really elevated our experience. The campsite was reasonably priced and was located on a beautiful property.

(photo: Greenwood Lodge and campground)

There are also several state parks with campgrounds in the area. The most convenient to Wilmington is Molly Stark State Park, which has two camping loops consisting of 23 tent/RV sites and 11 lean-to sites. The restrooms in Loop A have hot and cold water as well as token-operated showers. The restrooms in Loop B have running cold water. There are no RV hookups, but there is a dump available in the park.

Just west of Wilmington is Woodford State Park, which also has a campground. The park has four rental cabins, 76 tent/RV sites, 20 lean-tos, restrooms with flush toilets, hot and cold running water and coin-operated showers. Drinking water is available throughout the park. There is a RV sanitary station but there are no hookups.

Next, we enjoyed the proximity of Mountain Top Distillery, which is a Harvest Host. Their location is right next to 100 Mile View and has trail access to Mt. Olga Fire Tower. Just across the street is the Hogback and Mt.Olga Trailhead Parking, which allows for overnight stays with 48-hour parking. Please remember to leave no trace so future visitors can continue to enjoy this free boondocking location.

Hotels

One thing we love about Vermont is the quantity and quality of small businesses, and that extends to hotels and accommodations! In Southern Vermont, you’ll find several quaint, locally owned hotels, inns, and lodges, giving you a truly local and authentic experience. Although we didn’t stay at a hotel during our stay, we’ve researched some of the best accommodations in the area and organized them by their location:

Downtown Wilmington Accommodations

The Vermont House is located right in downtown Wilmington, Vermont, making it super convenient to explore downtown Wilmington. The property was built in 1856 and is listed on the National Historic Registry. While the building is historic and retains much of its original charm, the interior offers modern comforts.

The Nutmeg Vermont is located right in downtown Wilmington, Vermont. The Bed and Breakfast has a cozy outdoor fireplace, picnic area, and games room. Additional amenities include a hot tub, balcony, and spa bath. People rave about the breakfast served here!

The White House Inn is a high-end yet comfortable stay just east of downtown Wilmington. The property dates back to 1915 and has descendants of the Mayflower. The property also houses a great Italian eatery, Clara’s Cucina Italiana.

West Dover Accommodations

Deerhill Inn is a luxury Bed and Breakfast located in West Dover. The property itself is stunning inside and out, providing guests with a top-notch experience. From its sitting rooms with a log fireplace and breathtaking mountain views to the picturesque gardens and outdoor swimming pool, this accommodation really has it all.

Farm Road Estate is located in West Dover. This quaint and charming property has modern, rustic, and bright rooms. There’s also a seasonal pool on the property.

We love using Booking.com because they price match other competitor sites, ensuring we always get the best deal.

Unique Accommodations

This Mount Snow Yurt is a great option for those looking for a larger space since this Yurt has 3 bedrooms, 2 bathrooms, and sleeps up to 8 guests! It’s dog-friendly, has a large patio with a hot tub, and an arcade space. It’s located just outside of Dover!

This one-bedroom treehouse in Wilmington was built with wood from the property and looks super cozy! The deck has a barrel sauna, a cold or hot cedar soaking tub, a propane fire pit, a wood-burning chiminea fire pit, and a bar top for outdoor dining. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with DVDs, books, board games, chandelier, and dimmable lighting for any mood. This accommodation is truly a unique find in Wilmington!

There are also plenty of cozy cabins, which you can search for on VRBO.

Final Thoughts

From the quintessential small towns and friendly people, this region of Vermont has it all! After visiting Wilmington and West Dover, we can easily see why this Vermont destination needs to be added to everyone’s fall bucket list. With cozy and charming accommodations, ample camping options, and free boondocking in the Green Mountains National Forest, Southern Vermont is the perfect spot for a road trip, weekend getaway, or day trip!

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