Date Ideas in Windsor, VT

  • TripBuzz discovered 83 different types of activities for couples in the Windsor area, including Gardens (like Great River Outfitters & The Path of Life Garden), National & State Parks (like Mt. Ascutney State Park), Hiking Trails (like Brownsville Trail) and Breweries (like Harpoon Brewery), and much more.
  • We discovered a total of 96 date ideas in or near Windsor, Vermont, including 80 fun or romantic activities in nearby cities within 25 miles like Woodstock, Quechee, Ludlow and Killington.
  • TripBuzz discovered 83 different types of activities for couples in the Windsor area, including Gardens (like Great River Outfitters & The Path of Life Garden), National & State Parks (like Mt. Ascutney State Park), Hiking Trails (like Brownsville Trail) and Breweries (like Harpoon Brewery), and much more.
  • We discovered a total of 96 date ideas in or near Windsor, Vermont, including 80 fun or romantic activities in nearby cities within 25 miles like Woodstock, Quechee, Ludlow and Killington.
Showing 91-100 of 285
24.0 Miles
96% 85 votes
Theaters 703 Main St, Weston, VT 05161 MoreLess Info
Musical productions are the central focus of the Weston Playhouse that operates exclusively during the summer months of June, July, and August. The playhouse also has a cafe on-site that takes reservations for dinner and show arrangements.
24.0 Miles
100% 12 votes
Mountains RR 4, Killington, VT 05751 MoreLess Info
Guests can enjoy skiing, snowboarding, and other winter activities at Pico Mountain At Killington. Pico Mountain offers equipment rentals and lessons, and also houses the Vermont Ski and Snowboard Museum.
24.3 Miles
87% 522 votes
Food Shops Rte. 100, Weston, VT MoreLess Info
The general store of the past is brought to life at the Vermont Country Store that provides many hard-to-find and practical products. It has been family owned and operated for over 60 years.
24.4 Miles
90% 58 votes
Scenic Walks 456 New Hampshire, Newbury, NH MoreLess Info
The Fells Historic Estate and Gardens is an early 20th Century 22-room estate on over 80 acres of conserved land. A guide tour provides access to the house and history of John Milton Hay.
24.7 Miles
85% 33 votes
Skiing & Snowboarding 783 Townshend Road, Grafton, VT 05146 MoreLess Info
Seasonal recreation is offered at the Grafton Ponds Outdoor Center. In the winter, guests can enjoy skiing, snowshoeing, and snow tubing while summer has canoeing, swimming, hiking, and a variety of camps for kids.
24.9 Miles
100% 1 votes
Pond Appalachian Trail, Killington, VT 5751 MoreLess Info
Guests can enjoy fishing from the shore or aboard boats at Kent Pond. The pond offers boat ramp access and a shore fishing platform and features a large population of largemouth bass in addition to trout and sunfish.
25.8 Miles
92% 37 votes
National & State Parks 260 Ice House Rd., Londonderry, VT 5148 MoreLess Info
A year-round facility offering a variety of seasonal activities, Lowell Lake State Park is equipped with hiking trails for nature walks and snowshoeing in the winter. A nearby lake is also accessible for swimming, kayaking and fishing.
26.3 Miles
85% 34 votes
National & State Parks Rte. 100 1/2 mi north of U.S. 4, Killington, VT MoreLess Info
Giffords Woods State Park hosts recreational hiking trails through old growth forest and fishing spots at Kent Pond. Well-maintained campgrounds have fire pits, storage lean-tos, and areas for tents or RVs.
26.4 Miles
71% 7 votes
Waterfalls Wheelerville Road, Killington, VT MoreLess Info
Killington's McLaughlin Falls are stunning waterfalls that provide visitors with remarkable natural views. The surrounding woods are particularly scenic in the fall. A hiking and biking trail takes visitors right up to the falls.
26.6 Miles
81% 16 votes
Skiing & Snowboarding 615 Little Pond Road, Londonderry, VT MoreLess Info
The quintessential cross country ski experience is available at the Viking Nordic Center that offers a wide range trail system. The natural terrain provides both easy and difficult paths that are open to snowshoers and children skiers.
Showing 91-100 of 285
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