Fall Foliage

CHI-SE Corner New Paint FallCome to Vermont during the most gorgeous time of the year and stay at the historic Chester House while on your Fall Foliage vacation. Use the Inn as your home base for your touring and sightseeing in Nature’s dazzling Fall color palette.

Nestled in Vermont’s Green Mountains, quaint Chester is a magnificent place from which to view the brilliant Fall colors of the surrounding countryside. You can start and end some simply splendid autumn scenic drives in our little hamlet. We are more than happy to give driving directions and scenic tour routes to guests who are anxious to see Nature’s multicolored mountains and valleys in their Fall splendor.

When the Leaves Change

Click here for an animated map of Vermont’s leaf color progression in an average year.

  • The Fall Foliage period in any particular year can move up to 10 days in either direction of this average animation.
  • On the map, the Chester House is located near the southern edge of the second county up from the bottom (Windsor County), on the right side of Vermont.
Our front yard in the Fall
Our front yard in the Fall

If you want to intersperse other interesting activities among your leaf-peeping jaunts, there are lots of other things to do here during the Fall. Check our “Things-To-Do” page for a sampling of local Fall activities. Also, to make it easy for you, we have assembled for you a booklet of more than 165 places to visit and things to do nearby.

At the Inn itself you can relax and truly enjoy your stay. When you’re not taking in the leaves, sit for a bit in the wicker rockers on the front porch and just “watch the world go by” as the leaves find their way to the ground all around you.


The Inn is an easy drive from many East Coast states (see our location map). Folks travel here from from across the USA and from Europe, just to see Nature’s magnificent display of those vibrant Fall colors. In past years, guests from AL, AR, AZ, CA, CT, DE, FL, GA, IL, MA, MD, MI, NC, NH, NJ, NM, NY, OR, PA, RI, SC, SD, TX, VA, VT, WA, Canada, England and Germany have booked their rooms at the Chester House during Fall Foliage.


The Chester House is a favorite B&B for many leaf-peepers on their Fall trip to New England. Many folks have already reserved rooms for the next Fall Foliage Season.

So, we may not be hanging out our “Vacancy” sign very often during the coming Fall season. To avoid disappointment, we suggest that you select and reserve your room as soon as you set your travel plans.

We hope to see you during “sweater weather”!

PS: Don’t forget to bring your camera!


Client Testimonials

Interested in staying with us? Read some comments our guest's have left for us:

As always, we had a great time!  Thank you for everything.   See you both again soon!

Lynne and Danny O.

Fairfield, Connecticut

All your recommendations — from restaurants to ski rental to maple syrup — were so helpful… Finally, we were deeply touched by how welcome you made or 10-year-old son, Evan, feel. You made him feel special, smart and grown-up. This was an unexpected gift you so generously gave us. We wish you nothing but great success and hope to see you back on our next trip north to ski.

Lillie, Mark and Evan O.

Tenefly, New Jersey

As always, we had a great time!  Thank you for everything. See you both again soon!

Lynne and Danny O.

Fairfield, Connecticut

The Chester House has been a delightful home during my stay. Especially memorable are your culinary presentations and care shown to every guest.

You have both obviously devoted years on the decor, ambiance and historical presentations. Thank you for your T.L.C.

Pat E.

Concord, CA

Kathy and I just wanted to say thank you for your hospitality.  We loved our stay and had a great time checking out the area.  We even had fun finding the Hamilton Falls.   🙂  We look forward to staying at your B&B next year for our 31st Anniversary and really look forward to dining at Bella Luna again.

Ray & Kathy J.

Watervliet, New York

Thanks a million for everything, for all that you both did to make our stay in your inn an extra special time.  We appreciate so much the warmth and comfort we experienced.  Your gourmet breakfasts and attention to our needs was so much appreciated. as were your dining recommendations. God’s blessings on you both.  Hope to see you again soon.

Mary & Mario T.

Cortlandt Manor, New York

Just a note to thank you for our wonderful stay at the Chester House.  We all agreed it was one of the highlights of our vacation,  We love Vermont, your Inn, and your comfortable hospitality!

Deb, Freddie, & Chris L.

Ogden, Utah

We see that you finally received the much needed snowfall and we hope the skiers are all packing up their cars and heading your way. We wanted to let you know how much we enjoyed our stay in your beautiful, comfy Inn. The room (#7) was perfect for our 3-person family, and the morning breakfast sent us to the slopes every morning smiling, happy and quite full. We looked forward to coming back every night and sitting in front of the fire in the Keeping Room while we got our evening fix of Olympics.

Lillie, Mark, and Evan O.

Tenefly, New Jersey

Thank you for being a big part in making our first visit to Vermont a memorable and beautiful one for us. Your Bed & Breakfast is so charming and your love for detail is obvious.  We felt very comfortable in Room #1 and I loved hearing about the history of various pieces of furniture throughout the inn. And your delicious breakfasts were a perfect start for a day of exploring.  Thank you! Your warm and welcoming personalities make us want to come back soon.

Anke R.

Hyde Park, New York

Thank you very much for making our stay in Chester so special.  We had a wonderful time at the Chester House Inn and we plan on coming back for another visit real soon.

Danielle & Joey

Lindenhurst, New Jersey

On behalf of the Monitoring Team, I would like to thank you for your hospitality this week.  My team was very pleased with your establishment and the reports back to me during the week were glowing.  You were very gracious and flexible.  We will certainly recommend you to our co-workers and friends!

Judy C.

Vermont Department of Education

Thanks so much for your hospitality this weekend. My Mom and I had a great birthday weekend and enjoyed the cozy room.
We hope to see you again soon!

Libby F. & Ottile

Astoria, New York

This is an open recommendation to all first time visitors:

These innkeepers take your visit personally.  They talk with you, not to you and really want to make your stay special.  If our room is indicative of the others, it shouldn’t matter which one you select.  Warm, tastefully adorned and most comfortable.  The gathering room is inviting with a gently stoked, meticulously maintained fire.  Breakfasts are a hand-crafted, culinary delight.  This B&B is a value, period.

Bob and Jeri C.

Marlborough, Connecticut

I want to thank you or a wonderful weekend.  We had a very enjoyable, relaxing time the Chester House.  You made us feel like we never left home. You were fantastic hosts. We were a little sad to leave. Vermont is beautiful and we hope to see it in the winter time.  I will definitely spread the word about the Chester House to everyone I know.  The work and dedication you both put in to making everyone “feel at home” shows.  So we thank you again for a very enjoyable weekend.

Christine & Ralph

Deer Park, New York

Just wanted to thank you again for the great stay at the Chester House, loved breakfast… we are now thawing out back
in Maui, if you ever get our way, come stay with us. Aloha!

Janna and Richard H.

Maui, Hawaii

Sometimes when my mind is wandering I will find myself back at the inn.  I immediately get a warm and comforting feeling mainly because you both made two complete strangers feel so welcomed by your wonderful hospitality. 

Our best wishes.

Ken and Janis V.

West Haven, Connecticut