Honeymoons & Anniversaries

Day 1: Kick back

After checking into our romantic room or one of our suites, where your order of flowers and chocolates will await, relax in our garden or library, then go for a laid-back dinner at Worthy Kitchen. 

Day 2: Explore

Enjoy breakfast in bed or in our farmhouse dining room, then go on a picnic to Mount Tom, and visit Billings Farm and the Rockefeller Mansion. Complete your tour by a stroll through the village.

In the winter, go snowshoeing, then get a couple’s massage at the Woodstock Inn’s Spa.

Late afternoon, take a cooking class at Odyssey Events! Ever dreamed of wowing friends and family by enhancing your entertainment skills with your own staple dish? World-class restaurateurs Ted and Linda Fondulas will teach you anything you’d like in their beautiful Vermont home. BYOB, and enjoy your creation on site — a perfect ending to a perfect day! Be sure to book ahead of time (at a minimum, 24 hours in advance)

Day 3: Stretch your legs

Rent bicycles for self-guided mountain biking on Mount Peg and around town and local farms, or take it a notch further at Suicide 6 (don’t let the name scare you) for some more intense mountain biking. Ladies, look up their women-only clinics to conquer your fear and build a long-lasting enjoyment of the sport!

In the Winter, try fat biking, snowshoeing or cross-country skiing on the groomed trails of the Nordic Center.

In the evening, enjoy a romantic dinner at Simon Pearce in Quechee. Ask for a table near the falls, and be sure to visit the glass blowers one level below. 

Day 4: Discover Vermont’s micro-brews with a Brewery & Distillery Tour

Let a local guide pick you up after breakfast and drive you to several breweries, a distillery and a hard cidery. To learn more about this fabulous day-long tour, contact Vermontology directly.

Enjoy dinner at Max’s Tavern at the Barnard Inn, or walk to Richardson’s Tavern or the Red Rooster in town.

Day 5: Paddle away

Go kayaking on Silver Lake in Barnard or with Great River Outfitters in Windsor, or if you’re keen on getting up early, go fly-fishing with Wilderness Trails and The Vermont Fly Fishing School

In the Winter, go for the thrill of a Snowmobiling excursion.

In the evening, walk to town through the covered bridge and enjoy a relaxed cozy dinner at The Prince and The Pauper.

Day 6: Shop!

It’s time for some serious, curated shopping: Check out our list of Woodstock shops, and give special consideration to Shackleton Thomas, Farmhouse Pottery, Simon Pearce, and Andrew Pearce to start your collection of quality furnishings and appointments.

Dinner at Mangalitsa is a must when visiting Woodstock. You’ll be sure to have made reservations in advance, as this gem of a restaurant generally books out, and is only open Wednesdays through Saturdays.

Day 7: Soar

Kick off your life together by soaring to new heights! A balloon ride over the gorgeous Vermont landscape will show you things under a different perspective, and is certain to be a memorable part of your honeymoon.

In the winter, bundle up and go on a dog sled ride — another unforgettable experience.

These are just some ideas, and there are many other ways to enhance your honeymoon or anniversary celebration when visiting Woodstock! Please check our Things To Do Page. We think you will agree with us that Woodstock and the Woodstocker B&B are your ideal honeymoon location.
And as always, call or email for questions!