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Fall Pumpkin Display

From The Blog Photography in Woodstock

Shoot your Shot Photography locations in Woodstock

October has arrived and Fall has made its imprint, we have rounded up a list of the best well-known and some lesser-known locations to get the perfect Vermont Fall shot.

One of the most common questions I get during Fall is when is peak Fall Foliage in Woodstock? That is determined by Mother Nature but there is no doubt whenever you visit whether that’s during peak or not, Woodstock has so many destinations to get a postcard-worthy photo.

A combination of factors contributes to when Fall Foliage begins and reaches its peak, some of these include rainfall, temperature, light level, soil conditions, and more. I recommend following a Foliage Tracker for the most up-to-date on leaves starting their transformation.

Fall has blossomed as early as late September in Woodstock, and as late as the end of October. Most visitors come somewhere in the middle and New England rarely disappoints. Below we’ll give you locations any photographer would love with some hidden bonus areas.

October fall river view
Middle Covered Bridge fall foliage
Judy Laliberte
and Middle Covered Bridge!

always produce a classic photo op:

Middle Covered Bridge- In the heart of the Village, Middle Covered Bridge is beautiful (on both sides) and centrally located to everything in town. With craftsmanship and accessibility, this is a must-stop. Recently, craftsman, Jim Bradly added Cooper lanterns, giving it extra glow and detail when the sun is setting. *Note: This bridge includes a pedestrian walkway, so be sure to enjoy your stroll.

Sleepy Hollow Farm in autumn
Sleepy Hollow Farm is a photographer's dream

Sleepy Hollow Farm: A place of beauty in every season but most popular in the Fall, this is one of the most photographed farms in Vermont. Located on Cloudland Road this is on many photographers must capture lists when visiting. It’s been quite the Instagram-worthy spot right in our backyard, however, if you keep your eyes peeled Vermont has plenty of Instagram-worthy locations just as beautiful. Please be mindful of neighbors and your surrounding area when shooting. *Note: Remember that this is a private residence, please respect the signage and not cross property lines.

Fall Mt. Tom View
F.H. Gillinghams
Deep Fall Colors view from Mt. Tom

Faulkner Train, Mount Tom- A stunning aerial view of the town, not to mention a great Fall hike. You can see the town of Woodstock on one side and the green mountains lit up with autumn hues on the other. With a combination of fresh air and a rewarding view at the end, you can't go wrong with this choice. Enjoy your trek and incredible views of the town in Winter, Spring, Summer, and Fall. As a tradition Mt. Tom keeps its star shining brightly through winter, this hike will be worth the sweat when you get to the top.

Jenne Farm during fall foliage
Judy Laliberte
Jenne Farm...

Jenne Farm- This may be the most photographed farm in Vermont, out snapping even Sleepy Hollow Farm. Located in Reading, VT with its sweeping pastures and classic red barn, Jenne Farm is a gem to photograph. Note: This is a private residence and it’s recommended to come early and respect the private land marks while capturing your shot.

Woodstock Inn lawn foliage

Woodstock Inn front lawn- Coined Vermont's Most Beautiful Address! Across from Middle Covered Bridge and The Green you'll find the prettiest front lawn in all four seasons. Always manicured to the nines it's a popular photography destination. 

Wagon rides at Billings Farm during fall foliage
Judy Laliberte
Billings Farm offers plenty of photo-worthy perspectives

Local Woodstock photographer Stephanie Ambrose, gives us some of her own advice on what she looks for when trying to capture the perfect photo:

"Most of my photos are taken while out driving on the road (not while driving of course). I'll often pass a scene or composition that compels me enough to turn around the car. I also love to find creative ways to add depth of field to a's a fun personal challenge and hands-down my favorite way to add visual interest and complexity to an image......"

I love to capture anything that evokes a sense of nostalgia or desire for a certain time or place-these are probably the most rewarding kinds of images to capture.

Stephanie Ambrose

Lesser shared photo opportunities but just as stunningly beautiful

  • Old River Road-Take a drive and pull over for stunning views of the river, estate homes, tree-lined streets, and white fences
  • Downtown Cross Roads of Elm and Church Street- capture the bustling small town with shops, the Woodstock smiler, and a beautiful fall backdrop.
  • Quechee Gorge
  • Pleasant Street
  • Homes near Faulkner Park

For more insight on perfecting your Fall Foliage photos, read our insights and advice from artist and photographer Judy Laberte here.