Things to Do

After you arrive at the Chester House Inn you’ll probably want to plan the activities you want to experience and enjoy during your time in the Chester area.

Some folks just want to relax, “do nothing,” and simply get away from their everyday routine: read on the deck or in front of the fireplace, nap, walk around town, go out for a fine dinner, gaze at the stars, or watch the squirrels play. The phrase “take the day off” was invented here in Chester!

But if you’d like to get out there and enjoy Vermont’s many activities and sights, below is a listing of some of the types of things you can do. When you arrive at the Inn, we have waiting for you a detailed list of hundreds of local activities, showing locations, distances, driving directions, etc. Create your own itinerary and head out after breakfast with an exciting agenda for your day’s activities, sites and events. Head North or South one day, West or East the next.

Things To Do

Spring Summer Fall Winter
Go Antiquing and find those lost treasures from the past.
Take a Bicycle ride on our winding country roads and trails…rent or BYOB (Bring Your Own Bicycle).
Rent a boat and go Boating on the nearby rivers & lakes; or BYOB (Bring Your Own Boat).
Get a little taste of Breweries, Wineries and Cider Mills.
Visit Cheese & Maple Syrup producers: take home some of their tasty delights.
Visit Country Stores for some great buys and lots of interesting “stuff.”
Tour Vermont’s Covered Bridges, each different, each a picture.
Drop in on Crafters and Artisans; see and purchase their works.
Go Cross Country Skiing and glide across Vermont’s frozen tundra. Contact us to learn more about our “Cross Country Ski Package” to see how you can save on your lodging, on your Grafton Ponds Outdoor Center trail passes and on dinners at a fine local restaurant when you stay at the Chester House. Equipment rentals available.
Enjoy annual local events such as: “New Voices” (new author’s) Weekend (new author’s) Weekend (Jan.), Green Mountain Festival Series (Winter and Spring), Winter Carnival (Feb.), Maple Syrup Weekend (March), “Quilts Around the Town” Weekend (May), Yard-Sale Weekend (May), VT Crafters’ & Artists’ Open Studio Tour Weekend (May), Summer Free Outdoor Concerts (July & Aug.), Chester Craft Fair (late Sept.), Vermont Antiques Week (Sept.), Christmas Overture (Dec.).
Be astounded at the marvelous beauty of Mother Nature’s Fall Foliage that blankets the mountainsides.
Spend some time at local Farms, learn about animals and crops.
Enjoy the sport of Fishing in our local lakes and rivers.
Visit local Furniture makers and see their wares.
Feast your eyes at local Art Galleries. Maybe buy something for your living room wall?…
Take a swing at the ball at the many nearby Golf courses. Contact us to find out more on our “Golf Packages” to see how you can save on your lodging, on your green fees, your cart fees and on dinners at fine local restaurants, when you stay at the Chester House.
Go Hiking and get in touch with both Nature and yourself. We’ve let you know about some great nearby places to hike.
Stop by Historical Sites and get a better sense and understanding of our past.
Tour and shop in several nearby Historic Villages.
Ride ’em, Cowboy! Go Horseback Riding. Yee-haw!
Visit the famous Ben & Jerry’s Ice Cream Factory.
Enjoy Ice-Skating on the frozen lakes or at the town’s rink.
Practice your Indoor Golf swing, despite the cold outside.
Enjoy the exhileration of Motorcycling on Vermont’s scenic, rolling roads. If you’ve got a license, we can tell you where you can rent a Harley.
Take in the treasures to be found in local Museums.
“Shop ‘Til Ya Drop” in Outlet Stores. We’ve been offering a pre-Christmas “Holiday Shopping Package”. Contact us to find out more information.
Visit a Priory for some soul searching.
Learn the true meaning of “Being on rocky ground”: visit a Quarry.
If you like to Quilt, then visit some of the many nearby quilt shops…and we just happen to be right across the street from “Country Treasures,” one of the best quilt shops in New England. When they hold the “Quilts Around the Town” Quilt Festival, take advantage of our “Quilter’s Packages”. Contact us to find out more information.
Save on your lodging and on your lift tickets with our Stay & Ski Packages for downhill Skiing and Snowboarding at nearby Okemo Mountain Resort. Bromley, Magic and Killington Mountains are also close by. Contact us to find out more information.
Take a romantic Sleigh Ride “over the meadow and through the woods.”
Save on your lodging and on your lift tickets with our Stay & Ride Packages for Snowboarding at nearby Okemo Mountain Resort. Contact us to find out more information.
Sign up for a Snowmobile Tour for an hour or two in Nature’s Winter Wonderland.
Go Snowshoeing and glide across Vermont’s frozen tundra. Contact us to find out more information on our “Snowshoeing Package” to see how you can save on your lodging, on your Grafton Ponds Outdoor Center trail passes and on dinners at a fine local restaurant when you stay at the Chester House. Equipment rentals available.
Shop in Vermont’s many Specialty and Gift Shoppes.
Spend some relaxing time in State Parks, swimming, hiking, etc.
For some Broadway-quality Theater, take in the summer productions at the Weston Playhouse. Contact us to find out more information about our Theater Package.
Teddy Bears, Teddy Bears, and more Teddy Bears! You won’t tire of visiting the many Teddy Bear stops.
Ride the rails: “All Aboard” for a ride on the Green Mountain Railroad’s Antique Train.
Tour Nature’s Waterfalls and Gorges in our area.
Take a Wilderness Adventure to create, enjoy and respect a sense of harmony with nature, while challenging your mind and body: White Water Rafting, Kayaking, Mountain Biking, Orienteering, Rock Climbing, Rappelling, Caving, and Ice Climbing.

Client Testimonials

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Lynne and Danny O.

Fairfield, 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

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

Lynne and Danny O.

Fairfield, Connecticut

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