Consistently Named America's Most Beautiful Town, This New England Gem Thrives In The Fall
The U.S. has no shortage of picturesque towns that capture the imagination and inspire beloved Hallmark movie backdrops. From deep reds to bright yellows and golds, fall colors inspire nature enthusiasts to make the most of fall-related outdoor activities. Alongside pumpkin-picking, scenic hikes and drives, and grabbing a pumpkin-spiced beverage, leaf-peeping has emerged as a growing fall trend. Due to a rise in the popularity of leaf-peeping — the practice of admiring autumn foliage — an annual Fall Foliage Prediction Map has been introduced to help travelers track the changing colors of leaves across the country.
New England in particular, boasts some spectacular deciduous forest landscapes, where vibrant leaves transform during autumn. Conde Nast Traveler named Woodstock, Vermont, the Most Beautiful Town in America, while The Travel celebrated it for being particularly scenic. Home to just over 3,000 people, this idyllic town is stunning year-round thanks to its historic architecture and American charm, and is consistently regarded as being one of the most spellbinding in the northeast. But fall is when Woodstock truly comes alive, becoming an effortlessly photogenic autumnal wonderland. This region is perfect for getting outside and enjoying the changing colors of the season, with mild temperatures this time of the year, and minimal rainfall. Just be sure to book accommodation well in advance to keep your stay as budget-friendly as possible; Woodstock's small size means there are limited last-minute options for a fall vacation.
Outdoor activities to make the most of fall in Woodstock
Woodstock has a wide variety of hiking trails nearby, so make the most of your nature walks by keeping your pets on a leash and wearing appropriate footwear. The Mount Peg Trail is 2.5 miles long and can be done via foot or bicycle. Starting at Golf Street, take this route through gorgeous tree canopies and admire the fall foliage in all its glory. The trail culminates in a climb to the scenic viewpoint of Mount Peg, which rewards hikers with glorious sweeping vistas.
Woodstock also offers some breathtaking bike trails, thanks to the Woodstock Area Mountain Bike Association which maintains the area's mountain bike paths. The 13-mile-long Aqueduct Trail winds through woodlands and lakes, where mountain bikers of all ages can enjoy a range of courses with various difficulty levels, making it a perfect day out for families. If you don't have a bike, Woodstock Wheels offers e-bike rental for $110 a day. The route is also accessible for hiking.
National Parks are awe-inspiring in the fall, with protected natural spaces buzzing in vivid colors. Woodstock's Marsh-Billings-Rockefeller National Historical Park is a local gem, offering 20 miles of trails divided into seven routes. The park is open year-round and is free to enter, with a visitor center open from 10 a.m. to 5 p.m. Between May and November, the park offers guided tours with a park ranger for $9 for adults, $5 for seniors, and $1 for children.
Making the most of your visit to Woodstock
The great thing about Woodstock is that it is a small, walkable town with a compact center, making it perfect for browsing local small businesses. From gifts at Woody's Mercantile and clothes at Elevation Clothing to books at The Yankee Bookshop and flowers at Fleurish, there are plenty of quaint spots to indulge in a little retail therapy. Head to Central Street for a scenic stroll, grab a coffee at Mon Vert Cafe, or do some window shopping. If you park in the village center, be sure to have your ticket validated in a store for free parking.
With its rich history, aesthetic charm, and warm community spirit, it's little wonder Vermont is considered a perfect fall honeymoon destination. Whether you are engaged, married, or just looking to spend some quality time with your loved ones, you'll find no shortage of romantic fall activities. Book a couples massage at the Woodstock Inn & Resort Spa to unwind after a day hiking or biking. For an authentic farm-to-table dining experience, head to Cloudland Farm on a Friday or Saturday. Their on-farm restaurant is located just a 15-minute drive outside of town, and is a fantastic option for those wanting to sample seasonal dishes made from fresh, locally sourced ingredients. Be sure to book well in advance, as reservations can fill up two months ahead. It's important to note that the area has begun implementing road closures during fall foliage season in recent years to protect the property of residents — make sure to check before planning your trip to Woodstock.