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Want to take a unique and scenic getaway to Vermont? This Southern Vermont guide will help! Use it to plan a memorable Vermont trip focused on the outdoors and local finds in Brattleboro and Manchester, VT.

Outdoor portrait of black woman wearing a striped sweater with autumn leaves and trees in the background

Disclosure: This guide was created in partnership with Vermont Tourism. #ThisIsVT #FindYourVT

I’m passionate about adding nature to my vacations, so travel in Vermont is perfect for that! (Check out my Burlington travel guide as well to add to your research). 

It is very close to New York, my original home state, and essentially the same distance as popular upstate destinations like Lake George, NY – so why not try something new?

Use this guide to help you plan a stunning outdoorsy trip in Southern Vermont!

Fall foliage hike, looking up at trees

What to see + things to do in Southern Vermont?

Tips for the best activities to enjoy in Southern Vermont

Vermont is a great place to visit for access to mountain resorts, local produce (cheese!), scenic hikes, shopping, dining, and more. Its south gives you a charming small-town feel.

Southern Vermont is also ideal for road trips from large cities throughout New York, Connecticut, and Boston. You can also enjoy views of the Taconic Mountains and connect to the Long Trail (LT) which links Massachuttes to the Canadian border through Vermont’s Green Mountains.

If you want a quaint getaway filled with nature, dining, history, and relaxation—and don’t necessarily want a city vibe like Burlington offers, I recommend you venture around Southern Vermont instead!

view of Vermont estate from expansive gardens

How to get to Southern Vermont

Directions and best ways to get to Vermont

Southern Vermont is really accessible to several area cities. While road-tripping is the most common way to get around, I recommend planning your transport around Albany, NY as a base. This is perfect if you are driving, flying, or taking the train/bus.

For instance, you can take a plane or Amtrak train from Boston and NYC to Albany, NY. From there you can rent a car (which is what we did) or take a connecting bus.

Best time to visit Southern Vermont

Vermont activities based on seasons (all scenic things to do in Southern Vermont)

The best time to visit Southern Vermont is during the summer for warm weather and lots of outdoor activities. There is also October and November for cool hikes and pleasant temperatures, scenic drives, and fall foliage; and ski season.

Standing below the gondolas of Stratton Mountain

Things to do in Brattleboro, VT

Here are fun things to do in the Brattleboro, Vermont area.

Brattleboro is a laid-back, quiet town in Southern Vermont. It offers the opportunity to explore the state’s parks, taste award-winning cheese, and of course countless scenic photo spots. 

1. Hike to the Mt. Olga overlook at Molly Stark State Park

Molly Stark State Park is a small but welcoming hiking escape. During my 2022 visit, I arrived at their ranger station to pay the entry fee and was greeted by a banner reading “Park of the Year”, recognized by Vermont Parks & Recreation. 

There is a campground here and a loop trail to Mt. Olga. But don’t be fooled by the two miles of foot trails… this park has some incline and uneven terrain leading up to the lookout tower that stands at 2,418 feet. So there’s a bit of a fitness challenge.

Reading a trail sign on a hike in Vermont

2. Take epic photos at a foliage overlook

If you are excited to take scenic photos of Vermont, I highly recommend making time for an overlook shoot! I shoot with a Sony a7c but also took some great photos with just my iPhone!

Near the Molly Stark State Park is a fall foliage overlook along Route 9 at the Hogback Mountain Country store. There is plenty of boardwalk along the overlook and even a few tower viewers (those large, static binoculars you pay for at scenic viewpoints).

O. Christine overlooking Vermont fall foliage

3. Find local trails nearby like the Retreat Tower

A lot of people want to visit Vermont for its nature – and for good reason! There is so much woodland and lots of opportunities to pull over and hike a trail. 

This was the case with the stone Retreat Tower trail I checked out. It was a fairly short trail, but still somewhat steep at points so definitely gave a little workout. It is just down the road from Retreat Farm; its trailhead is across the street from the Harris Hill ski jump. I recommend using Google Maps to locate the trailhead because entry signage isn’t great. 

4. Eat award-winning local cheese—an essential thing to do in Southern Vermont

Visit the Retreat Farm to stop by Grafton Village Cheese Company for award-winning handmade, hormone-free cheeses from family farms. The retreat farm has several nature trails and even a kiosk that looks like a hobbit house. It offers free tastings from a distillery.

Standing outside of a cheese factory for tasting

5. Visit an orchard and try cider donuts

If you are visiting Southern Vermont during the fall, you have to seek out delicious cider donuts and fresh produce from a local orchard! I recommend Scott Farm Orchard, which is where I went. 

I purchased apple cider, and cider donuts, and did a tasting of their apples on display. There are also lawn games to play if you are there with family or friends, and a very clean bathroom to use (TMI, but not really because all that driving and hiking needs a bathroom break).

Sitting at a Vermon Orchard eating apple cider donut

6. Try Brattleboro, VT restaurants

We stayed in Brattleboro for one night and had dinner at Echo Restaurant & Lounge downtown, which I’d definitely recommend. 

One thing to note about Brattleboro restaurants is that things close early. We almost missed dinner because we assumed restaurants would stay open later, but these closed around 8:30 pm! So if good dining is one of the things to do in Southern Vermont that you cannot miss out on, plan ahead!

Things to do in Manchester, VT

Activities in Manchester worth trying!

7. Hike Prospect Rock Trail

Prospect Rock Trail is probably one of the most scenic hike overlooks in Southern Vermont, from my experience. The road is very straightforward but is also a steep uphill climb so be prepared!

It takes about 90 minutes to get to the viewpoint but it is totally worth it if you want panoramic views. We met a group of guys doing the LT hike, which they’ve been taking on for a few days annually for the last six years (instead of doing the trail all at once).

Expert Tip: finding the Prospect Rock trailhead was difficult since the road abruptly ends (you’ll see cars parked in the area) and there’s a rugged road that follows. A few minute’s walk beyond that rugged, steep road is the trailhead — so keep going!

Landscape view of oragne yellow and green leaves in Vermont for leaf peeping

8. Take a scenic gondola ride on Stratton mountain

What can be more gorgeous than relaxing on a gondola while enjoying 360-degree views!? Stratton Mountain Resort is less than 30 minutes from Manchester Village and their cable car tickets are for the whole day so you can go as often as you want. 

9. Visit Hildene, Lincoln Family Home

If you want a break from the adventurous (my calves needed a break from the climbs!) then Hildene is a great stop. You could take your time and be here all afternoon, honestly. 

This is the Lincoln family home – yes, that’s right, former President Abraham Lincoln. His eldest son lived here, and that’s where the family line ends! Stop by for views of the exquisite gardens, acres-long scenery, and a docent waiting to give you an oral recount of the property’s history.

10. Take a romantic horseback ride at Chipman Stables

You can’t possibly indulge in Vermont’s outdoor scene without a horseback ride! There are several stables around, and we got to take a private ride with a guide from Chipman Stables. 

My horse, Britches, did not like mud – just like me, haha. So it was hilarious to see all the ways she would try to get out of walking in a straight line. What a fun ride!

Woman waving hello on a horse in Vermont during autumn

11. Try restaurants in Manchester, VT

Take advantage of Manchester’s upscale culinary scene; lots to choose from!

Fair warning, though—make reservations because we got declined at 2 out of 3 restaurants we tried to eat at during the week. They were completely booked for dinners and one of them (The Silver Fork) said they were booked for the next few days.

Ultimately we took a late reservation at Ye Old Taverne (a historic restaurant serving regional fare in large portions); were able to walk in at the trendy Social House (Mediterranean-inspired cuisine, family style); and indulged at Depot 62 for authentic Turkish cuisine (we walked in for lunch and it was amazing!)

Scenic drives in Southern Vermont

Routes to drive for scenic overlooks

12. Route 30 between Brattleboro and Manchester, VT

Driving route 30 from Brattleboro into Manchester was one of my favorite drives in Southern Vermont – I totally recommend it! The winding road paired with the changing colors of the trees during autumn is definitely photo-worthy. 

I pulled over to a safe spot to take photos of an open field and hues of orange, yellow, and green leaves.

Vermont road with a lot of trees in yellow, orange, green colors

13. Kelley Stand Road to Stratton from Manchester 

For a true Vermont backroad experience, I recommend Kelly Stand Road during the warmer months (it is closed during winter).

Kelley Stand Road is a pretty dirt road to drive along if you are going to visit Stratton Mountain, as that’s where the gondolas are. You can kill two birds with one stone by enjoying the scenic drive and then enjoying the scenery from above in the cable car.

14. Mount Equinox skyline drive

Get your car brakes ready! Mount Equinox Skyline Drive is a privately owned property with a STEEP five miles of road leading you to nearly 4,000ft panoramic views of the Green Mountains, White Mountains, Adirondack Mountains, and more.

If you want to take on this adventure, I recommend stopping at each overlook on the way down to avoid overheating your breaks.

Standing in front of Mount Equinox sign for scenic drive

Which Stunning things to do in Southern Vermont caught your Eye?

I hope you loved these photos and tips about adventuring in Vermont’s southern region!

It is really cool that there are so many adorably scenic things to do in Southern Vermont, which you can do while supporting small businesses, local farms, parks, and establishments.

If you missed my video recap quickly highlighting my experiences in Brattleboro and Manchester, check out my Vermont Instagram post here. Enjoy!

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Hey Pinterest Fam!

Support parks and small businesses, and this list of Scenic Things to do in Southern Vermont, by pinning the image below to your planning board.

Pinterest image of Vermont foliage with text overlay that says Stunning locations in Southern Vermont


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