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Top 3 Fall Foliage Trips in Southern Vermont

Vermont foliage attracts thousands and thousands of tourists each year on leaf tours. And that's no coincidence. The yellows, oranges, reds and browns that paint the rolling mountains of Southern Vermont are worth the drive up - as attested by the legions of out-of-state plates that cruise its roadways every year.

Looking for the best fall foliage trips in southern Vermont? You've come to the right place. Throw out that GPS and let the maples, birch, oak, beech and elm trees be your guide. Here are our Top 3 Vermont Foliage Tours in and around the area.

1. The Quickie (Rte. 9, Rte. 8, Rte. 100 loop)

Approximate Drive Time: 50 Minutes

Start in the center of Wilmington, Vermont, heading west on Rte. 9. If it's early, grab yourself a cup of fresh roasted coffee at Bean Head's - best coffee in town. After about 7 miles, turn left onto Rte. 8. By now, you're well into the Green Mountain National Forest -- prime Fall foliage trips territory. This stretch is arguably the most colorful so keep your eyes peeled (if you're driving, please be careful, of course). Residences and commercial buildings are all but nonexistent - it's just you and the road. Turn left onto Rte. 100 North (if it feels like you're actually going south, that's because you are. Don't worry, the road curves northward in a bit). You'll have a fabulous view of Lake Whitingham on your left and Sadawga Lake to your right at one point - stay alert. Continue on 100 until you come back out onto Rte. 9. Take a left and you'll be back in Wilmington, just in time for a bite to eat at Maple Leaf Brewing.


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2. The Moose Hunter

Approximate Drive Time: 3 hours (small portion of route is unpaved).

Beebe Pond, Stratton, Vermont This Vermont foliage tour passes Beebe Pond on Kelley Stand Rd.

"The Moose Hunter" will take you down historic state roads, through quaint Vermont villages, over breathtaking mountain ridges and past ponds and streams teeming with wildlife. From Wilmington, head east on Rte. 9. In Brattleboro (a stop at Amy's Bakery on Main St. is highly recommended for fresh baked desserts, a sandwich, soup or hot drinks), head North on Rte. 30. After about 20 minutes, you'll pass through Newfane, VT, a quintessential New England village that seems straight out of a "Fall Foliage in Vermont" postcard. With a centuries-old courthouse, church, inn and general store, this hamlet is pretty much MADE for fall foliage pictures. Continue on 30, soaking in the view of Stratton and Bromley's colorful slopes along the way, to Manchester, a great place to stop and score some deals at various shopping outlets. In the center of town, turn left onto Rte. 7A. In Arlington, you'll need to make a few turns (see map for turn-by-turn directions) before getting to the main attraction: Kelley Stand Rd. Closed to traffic during the harsh winter months, this dirt and gravel road is a true nature lover's paradise. Don't be surprised if you spot a moose tramping through Beebe Pond [pictured above] on your right. Residencies are all but nonexistent on this 9-mile stretch, with only a few cabin-like camps here and there. The road eventually turns to asphalt again when it turns to Stratton-Arlington Rd. Follow this until you reach Rte. 100. Take a right and you'll cruise the remaining Vermont foliage tour miles in style, past Mount Snow and back to Wilmington.


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3. The Mass(achusetts) Attack

Approximate Drive Time: 1 hour 45 minutes

We'll depart slightly from a strict regiment of Vermont foliage tours, taking you briefly into Massachusetts. But we promise it will be worth it for the bright colors, winding roads and pit stop at one of Greenfield, MA's best food stops. Start by getting south on Rte. 100 out of Wilmington. In 15 minutes, you'll arrive in Jacksonville, VT, where you'll jump onto Rte. 112. Here to Greenfield is probably the best stretch of the ride for picture-perfect Vermont foliage, so keep your camera at hand. Once you've reached the thriving metropolis of Greenfield (it will feel like a metropolis after the peaceful solitude of Rte. 112), get yourself to People's Pint, a brewery and restaurant that serves its own fresh-brewed ales and locally-sourced dishes (try the pulled pork sandwich). When you're good and full, head north on Rte. 5 to Brattleboro. You can jump onto I-91 if you want to speed things up.


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Drive safely and enjoy Vermont's foliage and natural surroundings. If you're visiting the area for an extended stay, we'd love to host you in one of our short-term rental houses in Wilmington, Vermont.

Grout Pond, Stratton, Vermont Grout Pond near Stratton, Vermont

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  1. Patty Killion on

    [...] Don’t worry if you take a wrong turn or lose cell phone service while searching out covered bridges – asking locals for recommendations on which bridges to visit is perhaps the best way to do a covered bridge tour. Vermonters are very proud of the bridges, so you’re sure to get lots of advice and probably learn a bit of local history. If touring in spring and summer, you’ll see the Green Mountains in their glory, while the fall provides a backdrop of fantastic Vermont fall foliage. [...]
    • P.O. BOX 415, 9 Haystack Road, Wilmington VT 05363