Patio table with glasses full of beer
Let our knowledgable staff help plan your perfect stay

Judy’s Perfect Day

Imagine Your Day Going Something Like This

After a leisurely breakfast, we’d head out for a hike in the Madame Sherri Forest, hiking the Ann Stokes Loop up to Indian Pond. Then we’d go over to Brattleboro for a wander down Main Street, looking in on Sam’s Outdoor Outfitters, and Vermont Artisan Designs. We’d visit Grafton Cheese Company to buy a few of their fantastic cheeses to take home. When hunger struck, we’d enjoy lunch outside on the deck at Whetstone Station, right on the Connecticut River.

With the afternoon winding down, we’d come back to the inn, have a nap, and wake up with enough time to enjoy a glass of wine on the terrace while the sun is setting. Dinner in the candlelit dining room follows as a fitting end to the day. After dinner, we’d sit outside and look at the fireflies in the back meadow.

Let our knowledgable staff help plan your perfect stay

There’s So Much To Do Nearby

You’re guaranteed to find something to keep you busy with so many Southern New Hampshire attractions to choose from!

man hiking in New Hampshire

Outdoor Activities

Our Southern NH Inn is ideal for access to outdoor activities for all seasons in Vermont, Massachusetts, and New Hampshire. In warmer months, our staff can guide you to hiking, biking, kayaking, swimming, golf, tennis and horseback riding!

couple show shoeing in the mountains

Winter Sports

Winter in New Hampshire is the adventure seeker’s dream. Whether it’s skiing, snowboarding, snowshoeing, tubing or ice skating, you’ll find it here. But sometimes our favorite winter activity is curling up by the fire in your room at our country bed & breakfast.

apples and cider donuts

Farms & Tastings

Whether it’s apple picking at area orchards, maple syrup tasting at local sugar houses, or seeking out fine spirits at local distilleries, our quaint New Hampshire bed and breakfast is near it all. Let us help plan your savory escape!

fall colors in New Hampshire

Fall Foliage

Visitors from around the world come to New England to witness the majestic fall colors. This annual event only happens for a few months out of the year, which is why it’s important to grab your room early.

couple in a museum

Museums & History

There are an abundance of things to do in New England near the inn, including Historic Deerfield, Hildene Mansion, The Clark Institute, MASS MoCA, Brattleboro Museum of Art, and much more.

couple admiring a small town

Towns & Villages

Our area offers several distinct towns and villages to explore. In New Hampshire, we recommend visiting Keene and Walpole, and in nearby Vermont, you must see Brattleboro and Grafton. Chesterfield Inn is also the perfect home base for the ultimate getaway from NYC.

couple shopping holding bags

Shopping & Antiques

Lovely places to discover treasures are everywhere here! You’ll find unique shops including Vermont Country Store, Yankee Candle, Simon Pearce Glass, Ye Goodie ShoppeGreen Mountain Spinnery, and so many more!

jazz musician playing a saxaphone

Music & Theater

Enrich your life with the arts at one of our local establishments, including Latchis Theater, Sandglass Theater, Vermont Jazz Center, Brattleboro Music Center, Marlboro Music Festival and the Colonial Theater.

Fall foliage in Vermont

Judy’s Picks

Our innkeeper's favorite things to do in the area
  • Visit the ruins of Madame Sherri’s house and explore the Madame Sherri Forest in West Chesterfield.
  • Rent kayaks and paddle the Retreat Meadows and West River in Brattleboro, Vermont.
  • Wander the old fashioned Main Streets of Brattleboro and Keene.
  • Go cross-country skiing and snow tubing at Grafton Ponds, Vermont with lunch at the Grafton Inn.
  • Play a round of golf at Brattleboro Country Club, a classic New England golf course.
  • Snowshoe into Pisgah Park on the Kilburn Pond Loop off Route 63 in Chesterfield.
  • Hike Mount Wantastiquet for a bird’s eye view of Brattleboro, VT.
  • Drive up to Quechee, VT to Simon Pearce at the Mill, watch the glass blowing and have lunch at their restaurant.
  • Climb Mount Monadnock in Jaffrey, NH for a view that stretches to Boston.
  • Sample French Pastries and from scratch hot chocolate at Burdick’s in Walpole.
  • Visit Copper Cannon Distillery in West Chesterfield and taste their delicious spirits.
  • Drive 30 minutes to Historic Deerfield and take a step back into Colonial times.