Fall Foliage Weekend in Ludlow, Vermont: A Local’s 3-Day Itinerary

When it comes to choosing the perfect spot for a fall foliage getaway in Vermont, there are no wrong decisions.

Come early October, the mountains start to light up with those fiery reds and oranges that Vermont is known for. As the month progresses, the colors move down the mountains and creep southward and into the foothills and valleys.

Even though I’m a Vermonter, born and raised, and have spent just about every October in my home state, I love leaf-peeping as much as anyone I know.

I could wax on poetically for hours about my passion for October in Vermont, but instead, I’m going to talk about one of my favorite fall foliage getaways, a weekend based in the beautiful town of Ludlow, VT, with explorations in Peru, Londonderry, Weston, Plymouth Notch, and Killington.

This part of southern Vermont includes adorable small villages and gorgeous fall scenery, and it’s truly the perfect spot for a fall foliage weekend.

This itinerary includes a small section of Vermont Route 100. You’ll find plenty to do in this part of Vermont for an entire long weekend, but you can also make it part of a more extensive Route 100 road trip.

At-A-Glance Trip Planner: Fall in Ludlow, VT

• Best Time to Visit: Early to mid-October
• Where to Stay: Main and Mountain is a beautiful, independently-owned motel and bar within walking distance of shopping and restaurants.
• Nearest Airport: Albany International Airport is less than two hours from Ludlow. For more flight options, consider Logan International Airport in Boston, which is about 3.5 hours.
• How to Get Around: To really explore the area, you will need a car. Kayak is great for finding car-rental deals.
• Traveling with a dog? This is a very dog-friendly itinerary with dogs welcome on trails and in the Vermont Country Store.
• 3 Things to Pack: Rugged hiking shoes, a daypack, and the 10 essentials for hiking.

When is Peak Foliage in Ludlow?

Early to mid-October is a good rule to live by, but I’ve spent enough Octobers in the area to know that peak foliage depends on so much more than a calendar. Peak foliage is a gamble. To nudge the odds in your favor, here are some observations from the past few years, based solely on my own wanderings.

2025: higher elevations peaked the first week of October. Valleys were later, October 8-12.
2024: great color on October 16 in the valley. I did not make it into the higher elevations in ’24.
2023: bright colors on Okemo on October 13 with a few spots past peak. The valley was still colorful on October 17th, but fading.
2022: Colors seemed to peak early, October 7-9 in the mountains and 10-12 in the valley.

Why Ludlow, VT Makes an Ideal Home Base for Your Fall Vacation

The beautiful town of Ludlow is tucked in the Okemo Valley and surrounded by the Green Mountains. With just over 2,000 residents, Ludlow is probably best known as the home to Okemo Mountain Resort.

The village of Ludlow has enough restaurants and shopping to keep visitors enthralled for a couple of days, and the outdoor pursuits and attractions in the surrounding towns mean that you’ll never run out of things to do.

Since you’ll be exploring many of the towns and villages both north and south of Ludlow, I recommend making Ludlow your home base for your weekend getaway.

Ludlow VT Weekend Map

Here are the destinations covered in our Ludlow itinerary. Click on the box in the top right to open it in Google Maps.

Ludlow VT Lodging

If you’re traveling alone or with a small family, I highly recommend Main and Mountain as your home base. This small hotel is beautifully decorated, and you can choose from different room configurations depending on your needs.

Main and Mountain has a great little bar onsite, and it’s within walking distance of downtown restaurants. While you won’t find uber-cheap motel prices, Main and Mountain is quite affordable. We paid under $200 a night for a room during the fall foliage season, which is pretty hard to beat. Unfortunately, Main and Mountain is not dog-friendly.

If you’re looking for more room to spread out, this beautiful Ludlow home is dog-friendly, and it sleeps up to six people. It’s also got a great yard with a hot tub.

Day One: Okemo and Ludlow

Since you’ll be making your home base in Ludlow, it’s a great time to get to know the town and the surrounding mountains. Today’s explorations include a fantastic hike to the top of Okemo Mountain (or, if you prefer, a chairlift ride), explorations in downtown Ludlow, and a visit to beautiful Buttermilk Falls.

Hike the Healdville Trail to Okemo Mountain (Ludlow Mountain)

Start your weekend off right with a hike to a historical fire tower on the top of Okemo Mountain, also called Ludlow Mountain.

This is a six-mile hike (round trip) and gains about 2,000 feet of elevation. It will take you about four hours to do the whole thing, or at my confirmed slow-poke pace, closer to five, but the 360-degree views from the top of the fire tower make it well worth the effort.

From the roofed cab of the fire tower, you’ll have extensive views of the southern Green Mountains, the town of Ludlow, and Mount Ascutney.

This is a good hike for active dogs. Malinda enjoyed it, but I made her stay on solid ground while I climbed the fire tower.

If trekking up a mountain isn’t in the cards for this trip, you can also take a scenic ride on the Sunburst Six chairlift to the top of Okemo Mountain and hike down (or just ride back).

The chairlift runs until mid-October (usually Indigenous Peoples’ Day) and is $30 for adults and $24 for kids. Thursday to Sunday, 10 am to 5 pm. Dogs are not permitted.

Visit Buttermilk Falls

Buttermilk Falls is a series of three small waterfalls along the Branch Brook in Okemo State Forest. The falls are practically roadside but hidden from view down an easy, 0.2-mile trail.

The river is protected by the Vermont River Conservancy and cared for by the staff at Camp Plymouth State Park. This is one of the easiest waterfalls in Vermont to get to and also one of the prettiest to photograph in the fall.

The upper and middle falls both spill into fairly wide pools that are deep enough for swimming in the summer. In the fall, the river slows, making this a fun spot for rock hopping, picnicking, and enjoying a quiet afternoon.

Leashed dogs are welcome here, and my pup loves to swim under the falls.

Explore Ludlow Village

Ludlow is a tiny town in the Okemo Valley and is surrounded by the Green Mountains. If you’re staying at Main and Mountain, you’ll be within walking distance of shops, galleries, and restaurants — not too many, but enough to keep you busy for a few lovely hours.

Where to Eat in Ludlow

For a small town, Ludlow has enough great dining choices to keep you delightfully satisfied all weekend. Here’s what I’d recommend.

Breakfast: Go to the Hatchery at 164 Main Street for homemade cinnamon raisin French toast with real Vermont maple syrup! Throw in a mimosa (or a bacon Bloody Mary — you’re on vacation).

Lunch: Hit up Tacos Tacos for yummy and affordable American-Mexican fare in a tiny but colorful spot.

Dinner: Ludlow has a few really great dinner spots, but I almost always go to Homestyle Restaurant when I’m in the area. It never disappoints. I recommend making reservations as it’s not a big place, but you may also be able to find a seat at the bar if you’re passing through. Meals are served family-style, and the cocktails are divine!

Day Two: Plymouth Notch and Killington

Today, you’re heading north on Route 100 to explore one of Vermont’s most beautiful historic sites and tallest mountains. Charge up your phone or pack your camera because it’s a beautiful ride.

Visit President Calvin Coolidge State Historic Site

About 18 miles north of Ludlow, turn right on Route 100A and drive a mile to President Calvin Coolidge State Historic Site. Plymouth Notch is the birthplace and boyhood home of our 30th president, and his homestead and the surrounding village have been virtually unchanged since the 20th century.

The village is known as the Plymouth Notch Historic District and is on the National Register of Historic Places.

Meander around the 600 acres, visit the Calvin Coolidge Museum and Education Center, and check out dozens of historically preserved buildings.

Guided tours are offered daily, and you can see where Calvin Coolidge was born as well as where he was sworn into office on August 3, 1923, after the death of President Warren G. Harding the previous evening.

The historic site is open for the season through the end of October.

Be sure to stop at Plymouth Artisan Cheese for some samples while in Plymouth Notch.

Lunch at Long Trail Brewing

After leaving Plymouth, continue north on 100A to Bridgewater Corners, where you’ll find the famous Long Trail Brewing Company. 

This quaint riverside pub and restaurant is the perfect lunch spot, and the view is pretty great too! In addition to their popular Long Trail Ale, they make a variety of delicious seasonal craft beers that you won’t find in local stores.

The outdoor patio at Long Trail Brewing is dog-friendly.

Ride the Scenic Gondola to the Top of Killington Peak

Looking for far-reaching views that don’t know when to quit? Take a scenic gondola ride to the top of Killington Peak. At 4,241 feet, this is one of the highest peaks in Vermont.

The gondola ride is a quarter mile long, with 360-degree views, a small snack bar, and restrooms at the top.

In the fall, the Killington gondola is open Thursday to Monday from 10 am to 5 pm. Round-trip tickets start at $28 for adults and $21 for kids over 6. Kids 6 and under ride free. Dogs are not permitted.

Hike to Thundering Falls and Kent Pond

You don’t need to hike to Kent Pond; you can easily drive to the trailhead, get out of your car, and soak up the beautiful views. If you want to hike around the shore and onward to Thundering Falls, turn right into the woods when facing the pond.

The trail hugs the shoreline, and almost immediately, you will come to an inlet with several small waterfalls. Cross the bridge and continue on the Appalachian Trail.

When you get to Thundering Brook Road, continue along the Appalachian Trail to Thundering Brook Falls. It’s about 3.5 miles, round trip, and gains 400 feet of elevation. Thundering Falls is the sixth-tallest waterfall in Vermont. Dogs are welcome on this trail.

Day 3: Weston, Londonderry, and Peru

Today, you’re heading south to discover a few more of Vermont’s most adorable towns. Weston (population 623), Londonderry (population 1,919), and Peru (population 531) are all neighboring towns tucked in the mountains.

They are within a few miles of each other and so tiny that you can explore them all in a single day without having to rush.

Explore Lowell Lake State Park in Londonderry

Lowell Lake State Park is a quiet, undeveloped day-use park wrapped around a 102-acre lake, and in October it turns into a giant mirror.

The loop trail circles the entire lake for about 3.5 miles, mostly flat and easy, winding past stands of towering white pines, a Revolutionary War-era cemetery, and marshy inlets where the foliage doubles itself on the water. Go early, before the wind picks up, and you’ll get those glassy reflection shots that make everyone back home think you hired a photographer.

At my confirmed slow-hiker pace, this “little” 3.5-mile stroll somehow takes me the better part of two hours, mostly because I stop every hundred feet to insist that this is the best reflection yet. It is not a race. It is a leaf-peeping victory lap.

Dogs are welcome on leash throughout the park, and the flat, shaded loop is made for four-legged leaf-peepers, so bring the pup and let them do the sniffing while you do the gawking.

You can also drop a non-motorized boat in if you’ve got a canoe or kayak strapped to the roof. Paddling out into the middle of all that color is hard to beat.

Visit the Vermont Country Store in Weston

Weston is a picturesque New England village, complete with a little town green, a couple of cute stores, and the famous Weston Playhouse. Stopping in Weston is like taking a step back in time, so that’s what’s on the agenda.

Located across from the village green on Main Street, the Vermont Country Store is a destination you won’t want to miss. The aisles are stocked to the rafters with penny candy, maple syrup, apothecary items, household goods, and many local goodies.

Browse the crowded aisles and discover the largest collection of weathervanes in Vermont, the Vermont Scale Museum, and a year-round Christmas shop.

And speaking of Christmas, no matter what time of year you visit the Vermont Country Store, it’s always a good time to grab some one-of-a-kind Vermont gifts for your friends and family back home.

Lunch at JJ Hapgood General Store

Prior to a brief closure, JJ Hapgood General Store was once the longest continuously running general store in Vermont. Today, it is a vibrant fixture in the Peru community, and locals and visitors often come together to listen to live music, shop for provisions, and enjoy a delicious meal or coffee with friends.

Explore the bright interior stocked with gifts and groceries, or head outdoors and enjoy a meal on the marble patio. The coffee, sandwiches, and wood-fired pizza are delightful!

Hike Around Hapgood Pond

Two hikes in one day? Why not?

This tiny little pond makes an excellent spot for a picnic, leg stretch, or photo shoot in the fall. While Hapgood Pond is just 12 acres in size and 12 feet deep at its deepest spot, it’s a quiet retreat to enjoy the woods, the views, and a little solitude.

The hike around the pond is a mile in length, and there’s even a small campground. Campsites are $20 a night and can be booked on Recreation.gov through mid-October. Between October and May, all sites are first-come, first-served.

Where to Next?

Ludlow is centrally located, and if you’ve got more time to spend, consider one of these road trips or weekend getaways.

• Take a Route 100 Road Trip. Considered one of the most beautiful roads in Vermont, Route 100 travels from north to south through the Green Mountains for 216 miles. Five days is perfect for this road trip, but you can certainly do it in less. Start in Wilmington and drive north toward Canada.
• Take a Route 7 Road Trip. This is another weekend road trip that travels from Bennington north on Route 7 to Burlington, Vermont’s biggest city.
• Spend a weekend in Woodstock, Vermont. One of Vermont’s most beautiful towns in any season, Woodstock is especially magical in the fall.

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