Things to Do

Woodstock may be small from a population standpoint, but it covers a large area. With almost 62 square miles, it is actually the second biggest town in Connecticut.  There are a number of fun, unique and interesting things to do in town. 

Please note that the presence of any link anywhere on this site does not constitute an endorsement, favoring, or approval of the site or any specific commercial product, commodity or service by the Town of Woodstock.

Special Events

• Programs and Trips (Recreation Dept.)
• Artists Open Studios 
• Memorial Day Race (10K) and Parade on Memorial Day. Visit the Recreation Department to learn more.
• Fourth of July Jamboree on the green in East Woodstock
• Woodstock Fair, one of the oldest and largest agricultural fairs in New England, is held every year on Labor Day weekend, from Friday morning through Monday evening. Attendance averages more than150,000 people. Off-season events are also  held there.
• Roseland Cottage Arts & Crafts Festival (held the weekend after Columbus day in October each year) and summer evening concerts.

Shopping

• Shopping - antiques, crafts, florists, orchards, furniture makers, pottery, and more.
• Woodstock Grown - You can find a variety of locally grown or made products, including Christmas trees and seasonal greenery, honey, fresh fruits and vegetables, nursery and greenhouse products, dairy, wineries and fiber and yarn.

Dining

• The Inn at Woodstock Hill - 94 Plaine Hill Road, South Woodstock. Open for events.
• The Mansion at Bald Hill 29 Plaine Hill Road, South Woodstock. Elegant dining featuring seasonal menus.
• Woodstock Trading Post, formerly Sweet Evalina's Stand - 688 Route 169. Deli, groceries, ice cream, soups, wraps, grinders, salads, thin crust Italian pizza.
• Woodstock Grill and Pizza - 45 Route 171.
• Woodstock Valley Country Store - 1484 Route 171, Woodstock Valley. pizza, grinders, deli, snacks.

Places to Visit/Tours/Attractions - check websites for dates, times, fees and directions

• Cemeteries dating back to the 1700's.
• Fairvue Farms: a working dairy farm that offers tours seven days a week, and an observation area where you can watch milking in progress. MORE
• Libraries: Bracken Memorial, May Memorial, North Woodstock and West Woodstock.
• Palmer Arboretum, a lovely, small botanical park located on Woodstock Hill: education, enjoyment and enlightenment.
• Quasset School - a historical, early American one-room school house.
• Palmer Hall - Woodstock Historical Society, with a library, various historical collections, and period exhibits
• Roseland Cottage, a unique historic house you can tour, and a variety of special events.  Woodstock residents can tour the cottage for free!  The Recreation Commission also sponsors several free Summer Twilight concerts on the lawn from June - August.  See schedule.  The Cottage is an  excellent example of Gothic Revival Architecture. 
• Taylor Brooke Winery - and Taylor Brooke Brewery - Part of the CT Wine Trail, with tastings, tours and a gift shop. 

Outdoor Recreation

• Golf - Two public courses: Woodstock Golf Course and Driving Range across from Roseland Park ( 9 hole, with driving range [grass, mat], putting green, chipping, clubhouse pro shop and snacks) and Harrisville Golf Course, and Harrisville Golf Course (9 holes, pro shop, snacks). 
• Disc Golf - There is a new 18 hole Frisbee Disc Golf Course located at Crystal Pond Park!  Click here to read more about it!
• Lakes: Four lakes are accessible to the public: Muddy Brook Pond (also known as Pond Factory), Black Pond, Crystal Pond (Crystal Pond Park), and Roseland Lake.
• Little League
• Scenic drives - CT State Route 169.
• Trails and other Parks in town - there are a number of hiking trails at Crystal Pond Park, the Fifty-Acre Wood, Nipmuck State Forest, Palmer Arboretum, Roseland Park, Wyndham Land Trust, and more, offering varying degrees of difficulty and views. 

Parks and Campgrounds

• Crystal Pond Park - 120 acres on Crystal Pond. Swimming, picnicking, fishing, boating and ice skating; hiking, cross-country skiing, horseback riding; environmental education for youth and adults, including walks and talks; summer camping for youth and/or adults Rental of facilities to offset costs (weddings, graduation parties, family reunions, business picnics, etc.)
• Roseland Park -Playground, boating, skating, fishing, picnicking, walking and running. No swimming or camping is permitted. Pets must be leashed. Lake and grounds, pavilion, basketball court, benches, changing/bath house, boat launch. Rental: The park can be reserved for $75/day a day for weddings or parties.
• The Town Beach -Swimming, fishing, canoeing, and picnicking.  No pets are allowed. Swimming is "AT YOUR OWN RISK".  There are no lifeguards on duty. The Town Beach is also used for birthday celebrations, parties, and even weddings if desired.
• Camping: Woodstock has several public campgrounds, including Beaver Pines Campground, Chamberlain Lake Campground, and Solair (family-oriented nudist resort.)

Organizations/Clubs

• Theft Detection Society - the oldest, continuously active law enforcement society in the nation.
• The Quiet Corner Garden Club
• Woodstock Academy Alumni Association
• Woodstock Historical Society - periodic educational programs and exhibits, library and collection
• Volunteer! Woodstock has a number of boards and commissions. Volunteering is a great way to meet people, learn, and help shape the future of our wonderful town. Applications are available by clicking here. Contact the First Selectman's Office to learn more.