Nestled in northeastern Connecticut, Woodstock offers a charming blend of rural beauty and historical richness. This quaint town spans 62 square miles, making it the second largest in Connecticut.
You’ll find a variety of attractions and outdoor activities that make Woodstock an ideal destination for nature lovers and history buffs alike.
Woodstock’s past as a summer retreat for wealthy city dwellers has left its mark, with stunning 19th-century architecture dotting the landscape. You can explore this heritage at the Roseland Cottage, a beautifully preserved Gothic Revival house.
For outdoor enthusiasts, the Palmer Arboretum offers a peaceful escape, while the Town Beach provides opportunities for canoeing, kayaking, and fishing.
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How To Get To Woodstock
Getting to Woodstock, Connecticut is easy. You have several options for travel.
By car, Woodstock is accessible via major highways. Take I-84 or I-395 and follow directions to Route 169, which runs through the town.
If you prefer public transportation, take a train to Hartford. From there, you can catch a bus or rent a car for the final leg to Woodstock.
Flying in? The closest major airports are:
- Bradley International Airport (BDL) in Hartford
- T.F. Green Airport (PVD) in Providence, Rhode Island
- Logan International Airport (BOS) in Boston
From these airports, you can rent a car or use a combination of public transport and taxis to reach Woodstock.
For a stress-free trip, consider booking a private tour. These often include transportation from major cities like Hartford or Boston.
The journey is part of the adventure, offering scenic views of Connecticut’s countryside along the way.
What To See In Woodstock
Woodstock, Connecticut offers a charming mix of history and natural beauty. You’ll find plenty to explore in this quaint New England town.
Start your visit at Roseland Cottage, a stunning pink Gothic Revival house. This historic site showcases 19th-century architecture and landscaped gardens.
For nature lovers, Crystal Pond Park is a must-see. You can enjoy hiking trails, fishing, and picnic areas surrounded by scenic views.
Don’t miss the Taylor Brooke Winery. You can sample local wines and take in the beautiful vineyard scenery.
Woodstock is known for its farms. Visit Fairvue Farms to see a working dairy farm in action. You might even get to pet some cows!
If you’re lucky enough to visit in September, the Woodstock Fair is a highlight. It features agricultural exhibits, rides, and live entertainment.
For antique enthusiasts, Woodstock’s many shops offer treasures waiting to be discovered. You’ll find unique pieces to take home as souvenirs.
Orchards abound in the area. Pick your own apples or pumpkins depending on the season. It’s a fun activity for the whole family.
Where to Stay in Woodstock
If you know when you are planning to go but haven’t decided on accommodation, then use the map below to get an idea of which properties are available and to compare prices during the period you wish to travel.
Enter your proposed dates and use the ‘+’ to zoom in on a location and reveal more properties. Click on the price above a property to see more information.
(Please note that this selection will also include some vacation homes, AirBnBs, and VRBOs for those who are interested in that form of accommodation!)
History Of Woodstock
Woodstock’s story began in 1686 when settlers from Roxbury, Massachusetts founded New Roxbury. This community would later become Woodstock. The town’s early days were shaped by farming and small industries.
In the 1600s, John Eliot established “praying towns” for Native Americans in the area. The Mohegans also played a role in the region’s history.
Woodstock officially became part of Connecticut in 1749. Throughout the 18th century, it remained primarily a farming community.
The 19th century brought changes. Woodstock developed its share of industry, becoming known for shoe production. This era also saw the founding of important institutions:
- Woodstock Academy (1801)
- Woodstock Historical Society
Architecture from this period still stands today. You can admire Victorian Gothic Revival buildings like Palmer Hall. The Palmer Arboretum offers a peaceful spot to explore local flora.
For a glimpse into 19th-century education, visit Quasset School. The Bowen House provides another window into Woodstock’s past.
Woodstock’s rich history is evident in its well-preserved buildings and landscapes. As you explore, you’ll feel connected to the town’s centuries of stories.
Towns Near Woodstock
Woodstock is surrounded by charming New England towns. You’ll find plenty to explore within a short drive.
Putnam, just 15 minutes away, offers antique shops and riverside dining.
Its historic downtown is perfect for a leisurely stroll.
Thompson, to the northeast, boasts scenic views and hiking trails. You can enjoy outdoor activities at West Thompson Lake.
Pomfret, west of Woodstock, is known for its rolling hills and farmland. Visit the Sharpe Hill Vineyard for wine tasting.
Eastford, to the south, provides a quiet escape with its rural landscapes.
The Natchaug State Forest is great for hiking and fishing.
Union, the smallest town in Connecticut, lies northwest. It’s home to Bigelow Hollow State Park, ideal for boating and picnicking.
Ashford, southwest of Woodstock, features the Paul Newman’s Hole in the Wall Gang Camp.
The nearby Mansfield Hollow State Park offers hiking and water activities.
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