Experiencing a New England autumn should be on everyone’s Bucket List! Now you can fully experience the breathtaking joys of foliage, crisp air, sweet treats, and outdoor adventure in New Hampshire with this extensive itinerary we have specially crafted just for you – our wonderful guests! And if you haven’t yet joined our family, now is the perfect time to plan your first trip to our New Hampshire bed and breakfast in the charming town of West Chesterfield and experience the breathtaking beauty New Hampshire for yourself.

Beautiful Foliage in New England

Hurry and book soon for the upcoming autumn season. We are already filling up fast for this peak time of year! Specifically, October is the absolute best time to view stunning fall foliage in New Hampshire. Choose your favorite room and book while you still can. Then check “Experience New England Fall” off your bucket list!

Romantic Lodging in Chesterfield

Luxurious Accommodations at Our Inn

DAY 1 – BREATHTAKING FOLIAGE UP CLOSE

  • Admire the red and orange foliage as you drive up to our charming New England inn. Walk in with your bags and enjoy the warmth of the toasty air from the fireplace that feels peaceful and cozy after being outside in the crisp fall weather. Leave your bags in your romantic room where you will be spending the next three nights, and then head back out to the lobby to relax by the fire before you explore the area. You are finally beginning your fall New England getaway, soak it all in!

Look for Our Favorite Covered Bridges During Your Trip

  • Get the lay of the land with a self-guided foliage tour. Drive around and admire the magic of brilliant reds and oranges, with a bit of yellow that fill the trees and saturate the landscape with color. It’s like being in a postcard and is an experience you won’t forget. We recommend seeking out some charming covered bridges for an even more picturesque experience. Check out the West Dummerston Covered Bridge, Brattleboro Creamery Bridge, and 4 Covered Bridges all in Swanzey, NH. See how many you can find – and don’t forget to bring your camera!

Get Lost in the Corn Maze Together

  • Embrace your inner kid and get lost in a corn maze together. One of our favorite places to do this is the fun Corn Maze at Gaines Farm in Guilford, Vermont. Each fall season, Gaines Farm offers a maze consisting of 7 acres of ten-foot corn stalk – they describe it as “Maize madness that will mystify, and entertain!”

Fall in Love in New England

  • Celebrate the beginning of your wonderful autumn trip together with cocktails at Twenty One Bar and Grill in Keene, New Hampshire. Then head to The Stage Restaurant for a fabulous dinner out. Start with some scampi casanova & bread to share, follow it up with seared salmon, black diamond steak, or lamb chops, and then close out your night with a rich slice of cheesecake.

Cozy & Romantic Nights at the Inn

  • After a wonderful afternoon out, head back to the inn to cuddle by the fire place and then retreat to your room for a cozy and oh so comfortable night sleep.

DAY 2 – EXPLORING THE AREA

  • Wake up after a peaceful and cozy night in your warm and romantic room and enjoy a full breakfast and a steaming cup of hot coffee.

Experience Local Flavor at the Grafton Cheese Company

  • Get a true taste of local flavor with a visit to the Grafton Cheese Company in Brattleboro, Vermont. Sample from a great selection of local cheeses with a focus on their award winning cheddars – delicious! A visit during the week will include an opportunity to watch their very own cheddar being made at the viewing area. Don’t miss it!
  • While you’re out, grab lunch in Brattleboro at The Porch Too on Putney Road (owned by our friends!). Fresh local soups, salads, sandwiches, and more are all delicious. This is a wonderful chef owned restaurant with great imaginative food. Be sure to try the Vietnamese Chicken Salad!

Alyson’s Orchard – Photo by Fran Imhoff

  • A fall day in New Hampshire isn’t complete without a delightful afternoon at Alyson’s Orchard in Walpole, NH. This lovely orchard offers spectacular views, delicious apples of all kinds, and so much more. Pick your own is so much fun!

Photo by Kendal J. Bush Photography

Photo by Kendal J. Bush Photography

  • After enjoying all of these activities, come back to the inn and enjoy a glass of wine or a cocktail on the terrace. If it’s chilly, there will be a fire in the fireplace in the living room. Plus, 10 of our rooms have fireplaces so you can enjoy your own fireplace, in the privacy of your room. Our Autumn menu always features the bounty of the season, such as maple glazed stuffed acorn squash, grilled wild games sausages, cider brined duck breast, and local cheeses. It will be divine!

Gorgeous Hikes with Breathtaking Views

DAY 3 – OUTDOOR FUN (& Beer!)

  • The best way to enjoy the beautiful foliage is to go into the woods and get up close to the leaves! Here are some favorite spots among the locals…
    • Mount Wantastiquet in Brattleboro, Vermont with expansive views of the West River Valley
    • Green Mountains Ann Stokes Loop in West Chesterfield and the Madame Sherri ruins in the loop (the perfect place to stop on your way into the woods)
    • Chesterfield Gorge in Chesterfield, NH
    • Mount Monadnock in Jaffrey NH is a strenuous climb, but so worth it! On a clear day you can see Boston! If you’re up for the challenge, we highly recommend it.

Photo Provided by Whetstone Station

  • After a day of being active in the woods and before you head back to the inn for the night, go to the wonderful Whetstone Station! This establishment is owned by our very own friends and is a wonderful atmosphere and setting with a fantastic selection of their own beers, made there, and beers from around the world, you are sure to have a great time. An extra special touch is the incredible view of Mount Wantastiquet and the Connecticut River. The best vantage point is from their beer garden on the roof or from a bar stool at the bar on the first floor.

An Autumn Stay’s Not Complete Without Local Treats

DAY 4 – GOOD EATS AND SWEET TREATS

  • After you enjoy another wonderful breakfast at the inn, set out on a search for the best seasonal treats. Your first stop should be Allen Brothers in Westminster, Vermont for fresh apple cider and just made apple cider donuts coated in cinnamon sugar. They are incredible! You have to taste them for yourself.

There Are Many Seasonal Goodies to Check Out

  • Walker Farm in Dummerston, Vermont is also a terrific local place that you must visit! They have pumpkins, gourds, gorgeous big buckets of mums, and more! Spend some time meandering around and enjoying all there is to see. Then
  • Pack up and head home with all of your souvenirs and lasting memories!

If traveling to New Hampshire this fall isn’t possible for you, plan a trip for next summer! View our New Hampshire Summer Itinerary.