Things to Do in Woodstock Connecticut

Explore Roseland Cottage

One of the standout attractions in Woodstock, Connecticut is Roseland Cottage. This historic house museum is an outstanding example of Gothic Revival architecture.

Visitors can tour the beautiful gardens, see the bowling alley, and appreciate the unique interiors of this well-preserved 19th-century home.

Roseland Cottage often hosts events and concerts, making it a bustling hub of activity throughout the year.

It is a great place to get a sense of local history while enjoying meticulously maintained grounds.

Hike at the Pulpit Rock Road

Pulpit Rock Road is a fantastic spot for hiking enthusiasts in Woodstock. This location offers trails that cater to all skill levels, from gentle walks to more challenging hikes.

The trails are well-marked and provide breathtaking views of the Woodstock area, making it a perfect spot for nature lovers and photographers alike.

Hiking here during the fall provides a stunning display of New England’s famed autumn colors.

Family Fun at Woodstock Fair

The Woodstock Fair is an annual event that families will not want to miss. Held every Labor Day weekend, this fair features everything from agricultural exhibits to carnival rides.

It’s a wonderful way to experience local culture, try regional foods, and enjoy live entertainment.

For those interested in petting zoos and livestock shows, the Woodstock Fair offers an in-depth look at rural life.

Early arrival is recommended as the fairgrounds can get quite crowded, especially on sunny days.

Visit the Palmer Arboretum

The Palmer Arboretum is a hidden gem in Woodstock that offers a peaceful retreat for anyone looking to unwind. This beautifully maintained arboretum showcases a variety of tree species.

It’s a wonderful place for a leisurely stroll, bird watching, or simply enjoying a picnic in serene surroundings.

The Arboretum is open year-round and is particularly lovely in spring when flowers are in full bloom.

Art and Culture at The Woodstock Academy Art Show

The Woodstock Academy hosts an art show that highlights the talents of local artists. This event is perfect for those interested in visual arts, sculpture, and crafts.

It’s an excellent opportunity to meet local artists, purchase unique artwork, and support the local art scene.

The event usually occurs in spring and is a must-visit for art aficionados.

Savor Local Cuisine at Sweet Evalina’s Stand

Sweet Evalina’s Stand is a go-to spot for delicious local cuisine. This local eatery offers comfort food like pizzas, burgers, and a variety of homemade pies.

The relaxed atmosphere and friendly staff make it a great spot to enjoy a meal with family or friends.

It’s open for breakfast, lunch, and dinner, but be sure to try their breakfast options as they receive rave reviews.

Discover History at The Woodstock Historical Society

The Woodstock Historical Society provides a deep dive into the area’s rich past. Their exhibits feature artifacts, photographs, and documents that tell the story of Woodstock through the ages.

For history buffs, this is an unmissable stop that offers valuable insights into the town’s development and significant events.

The historical society also occasionally hosts lectures and educational programs.

Tranquil Day at Crystal Pond Park

Crystal Pond Park is a wonderful destination for those seeking tranquility and natural beauty. The park features a lovely pond, making it a great spot for fishing or kayaking.

Picnic areas are available, and the park is often less crowded, providing a peaceful setting for relaxation.

This is also a great spot for bird watching, with a variety of species frequenting the area.

Visit Taylor Brooke Winery

Wine aficionados will enjoy the offerings at Taylor Brooke Winery. This winery features a range of handcrafted wines that showcase the best of the local terroir.

The tasting room is inviting, and the staff are knowledgeable, making it a pleasant experience for both seasoned wine lovers and newcomers.

Taylor Brooke also hosts events and has a lovely outdoor area for sipping wine while enjoying the scenic views.

Solar Stage Art and Music Festival

Solar Stage Art and Music Festival is an annual event that brings together musicians and artists from all over. It’s a lively weekend filled with live performances, art installations, and workshops.

This festival is a great way to immerse yourself in Woodstock’s vibrant arts scene and meet like-minded individuals.

The festival caters to all ages and is family-friendly, with activities and entertainment options for children as well.

Cycling on the Airline State Park Trail

The Airline State Park Trail is a fantastic route for cyclists. This extensive trail offers scenic views and a mix of paved and unpaved paths, making it suitable for various cycling preferences.

The trail runs through multiple towns, including Woodstock, and is perfect for long, leisurely rides or more intense cycling workouts.

This is an ideal spot for a day outing with family or friends, picnic stops included.

Book Shopping at The Copper Fox

The Copper Fox is an independent bookstore in Woodstock that is adored by both locals and visitors. This cozy store offers a wide selection of books, from bestsellers to hidden gems, across various genres.

The knowledgeable staff are always on hand to provide recommendations or help you find what you’re looking for.

The Copper Fox also features a small café, perfect for enjoying a cup of coffee while diving into your new book.

Adventure at Woodstock’s Annual Scarecrow Festival

The Annual Scarecrow Festival is a fun and quirky event that brings the community together. Participants create and display scarecrows, each with unique and creative designs.

It’s a fun activity for families and a great way to kick off the fall season.

The festival also features live music, food vendors, and activities for kids, making it a lively community event.

Relax at Woodstock Orchards

Woodstock Orchards is the perfect destination for a laid-back day of apple picking. The orchard offers a variety of apple species and is charming to visit in the fall.

Besides apple picking, visitors can purchase fresh produce, baked goods, and enjoy some apple cider donuts.

The friendly atmosphere and delicious offerings make it a popular spot among locals and visitors alike.

Engage in Food and Drink at the Roseland Park Farmer’s Market

The Roseland Park Farmer’s Market is a must-visit for anyone interested in fresh, local produce. Held during the warmer months, the market features a variety of vendors offering everything from vegetables to handmade crafts.

It’s a great place to buy organic produce, artisanal cheeses, and other local specialties.

Supporting this farmer’s market helps sustain the local economy and provides high-quality, fresh foods for your family.

Scenic Drive on Connecticut Route 169

One of the most picturesque ways to explore Woodstock is by taking a scenic drive on Connecticut Route 169. This National Scenic Byway offers charming views of New England’s countryside.

The route is lined with historic landmarks, quaint homes, and beautiful landscapes, making it a delightful drive any time of the year.

Autumn is a particularly popular time to take this drive due to the spectacular foliage that paints the scenery in vibrant hues of red, orange, and yellow.

Along the way, you’ll also find several antique shops and local eateries where you can take a break and soak in the small-town charm of Woodstock.

Stay at The Inn at Woodstock Hill

If you’re planning an overnight stay, The Inn at Woodstock Hill offers a charming and comfortable lodging option. This historic inn provides beautifully appointed rooms and excellent service.

The inn’s restaurant is widely praised for its delicious meals, making it a convenient spot for dining if you’re staying the night.

Guests love the peaceful ambiance, friendly staff, and the beautiful surroundings of the property.

It’s an ideal place for a romantic getaway or a serene retreat away from the hustle and bustle of city life.

Pros

• Charming and historic ambiance
• Excellent restaurant with highly praised meals
• Peaceful and scenic surroundings

Cons

• Limited availability during peak seasons
• Higher rates compared to other local lodging options

Enjoy Craft Beer at Black Pond Brews

For craft beer enthusiasts, Black Pond Brews is a must-visit. This local microbrewery offers a variety of craft beers that are well-loved by locals and visitors alike.

The brewery often releases seasonal and limited-edition brews, so there’s always something new to try.

The laid-back atmosphere and friendly staff make it a great spot to unwind and enjoy a cold beer.

Black Pond Brews also hosts events and live music, adding extra fun to your visit.

Explore Woodworking at The Sharpening Stone

For those interested in woodworking, The Sharpening Stone in Woodstock offers something unique. This shop provides high-quality tools and equipment for woodworking enthusiasts.

The knowledgeable staff can help you find the right tools and offer advice, making it a great resource for both beginners and experienced woodworkers.

They also offer workshops and classes, allowing you to learn new skills and techniques in a hands-on environment.

Pros

• High-quality tools and equipment
• Knowledgeable staff
• Workshops and classes available

Cons

• Specialty shop with potentially higher prices
• Limited store hours

Seasonal Activities at Woodstock Orchards

Woodstock Orchards is a lovely place to visit year-round, but it particularly shines during the fall season. During this time, they offer apple picking, a fun and family-friendly activity.

The orchard has a variety of apples to choose from, along with freshly made apple cider and donuts that are a hit among visitors.

They also offer pumpkin picking and hayrides, making it a great outing for the whole family.

Make sure to check their schedule for special events and seasonal activities to plan your visit accordingly.

Relax at Roseland Lake

Roseland Lake is another tranquil spot in Woodstock where you can enjoy a day out in nature. The lake is ideal for kayaking, fishing, and picnicking.

It’s a peaceful location that is perfect for spending time with family or friends, especially if you enjoy water-related activities.

The lake is surrounded by beautiful scenery, making it a perfect spot for photographers and nature enthusiasts.

You can also take a leisurely walk around the lake to fully appreciate its serene beauty.

Woodstock’s Local Boutiques and Shops

Woodstock boasts a number of charming local boutiques and shops. From antique stores to handcrafted goods, there’s something for everyone.

The Sunshine Shop is a popular boutique that offers a variety of unique gifts, home decor items, and handmade crafts.

Paying a visit to these local shops is a great way to support small businesses and find one-of-a-kind items that you won’t see anywhere else.

Plus, it’s always fun to chat with the shop owners and learn more about the stories behind the products they carry.

Yoga at the Copper Beech Institute

If you are looking to relax and revitalize, the Copper Beech Institute offers excellent yoga and meditation classes. This institute is dedicated to holistic health and mindfulness.

You can participate in various classes and workshops that help improve physical and mental well-being.

The serene environment and experienced instructors make it an ideal place for both beginners and seasoned practitioners.

Yoga is a fantastic way to relax and find inner peace, making your visit to Woodstock even more rejuvenating.

For more options in holistic health and yoga, you might want to check out these leading yoga retreats in Rhode Island.

Immerse Yourself at The Vanilla Bean Cafe

The Vanilla Bean Cafe is a beloved spot in Woodstock that offers great food, coffee, and local music. Their menu features a mix of delicious breakfast, lunch, and dinner options.

Live music performances are often held on weekends, providing a cozy and entertaining dining experience.

The relaxed atmosphere and friendly staff make it a favorite among both locals and visitors.

Be sure to try their homemade desserts, as they receive rave reviews.

Woodstock Summer Concert Series

The Woodstock Summer Concert Series is a fantastic way to enjoy live music in an outdoor setting. Held at the Roseland Park, this series features performances by local and regional bands.

The concerts are family-friendly and make for a fun evening out during the warmer months.

Feel free to bring a picnic, lawn chairs, and blankets to fully enjoy the experience.

It’s a great way to relax, listen to good music, and spend quality time with friends and family.

Explore Historic Cemeteries

For history enthusiasts, exploring Woodstock’s historic cemeteries can be a fascinating experience. The Old Trinity Church Cemetery and the North Woodstock Cemetery are two spots that offer a glimpse into the past.

The gravestones here date back to the 18th and 19th centuries, and some interesting sculptures and inscriptions provide a peek into local history.

These cemeteries are quiet and peaceful places for a contemplative walk and to reflect on the town’s heritage.

Just be sure to be respectful during your visit to these historic sites.

Biking on Thompson Road

Thompson Road is another fantastic route for biking. This scenic road offers gentle hills and picturesque views, making it a popular spot for both casual riders and serious cyclists.

You can enjoy a peaceful ride surrounded by nature, with various spots to stop for photos or a picnic.

The road is well-maintained and doesn’t see heavy traffic, providing a safe environment for biking.

This is an ideal activity for anyone looking to enjoy the outdoors and get some exercise.

If you’re interested in more outdoor adventures like this, you might want to explore some premier hiking trails in Rhode Island as well.

Annual Putnam River Fire

Though not directly in Woodstock, the nearby town of Putnam hosts an Annual River Fire event that is worth a visit. Held during the summer months, this event features bonfires along the Quinebaug River.

The river is lit up with fire pits that create a magical ambiance, accompanied by live music and food vendors.

It is a short drive from Woodstock and makes for a great evening outing.

It’s an enchanting experience and provides a unique way to enjoy a summer night with family or friends.

Farm to Table Dining at The Golden Lamb Buttery

For a memorable dining experience, The Golden Lamb Buttery offers farm-to-table cuisine in a rustic setting. This family-owned restaurant is situated on a picturesque farm and serves fresh, locally-sourced dishes.

Guests love the unique ambiance, with rustic barns and beautiful views of the countryside.

The restaurant is known for its delicious food and excellent service, making it a special place for a romantic dinner or a celebratory meal.

Reservations are recommended as it is quite popular among both locals and tourists.

Exploring Woodstock Academy

Woodstock Academy is not just a school; it is a landmark in its own right. The historic campus, with its beautiful buildings and well-maintained grounds, is worth a visit.

Visitors often find the architecture and history of the academy fascinating. Sometimes, guided tours are available, offering insights into the school’s past and present.

It’s a wonderful place to explore, especially if you’re interested in education and history.

Additionally, the campus frequently hosts events, making it a hub of cultural and educational activities in the town.

Attend a Workshop at the CT Audubon Society Center

The Connecticut Audubon Society Center in nearby Pomfret offers wonderful workshops and events for nature lovers. These activities include bird-watching tours, nature walks, and educational seminars.

The center is dedicated to conserving Connecticut’s environment through education, and its programs are suitable for all ages.

Participating in these events is a great way to learn more about the local flora and fauna. It also allows you to engage with like-minded individuals who share a passion for nature and conservation.

The staff and volunteers are very knowledgeable and passionate, ensuring a rewarding experience for all visitors.

For additional family-friendly outdoor activities, consider exploring some leading attractions for family fun in nearby Rhode Island.

Gardening Tips and Inspiration from Pomfret Garden Co-op

Just a short drive from Woodstock, the Pomfret Garden Co-op offers a treasure trove of gardening supplies and plants. This co-op is perfect for gardening enthusiasts looking to spruce up their outdoor spaces.

The knowledgeable staff are always available to offer tips and advice, making it a great resource whether you’re a beginner or a seasoned gardener.

The co-op also hosts workshops on various gardening topics, from organic gardening to pest control, giving you the opportunity to learn new skills and techniques.

Visitors particularly appreciate the variety of plants available, including rare and heirloom varieties.

Woodstock’s Eclectic Antique Shops

If you’re a fan of antiques, Woodstock will not disappoint. The town is home to several antique shops offering unique and fascinating finds.

The Woodstock Trading Company is a popular spot, known for its eclectic collection of vintage items ranging from furniture to collectibles.

Another notable shop is The Barn at 17 Antiques, which features a wide range of items from different periods, meticulously curated by the owners.

Antique shopping in Woodstock is not just about finding rare items; it’s also about the stories and history that come with each piece.

Attend the Annual Woodstock Christmas Bazaar

The Annual Woodstock Christmas Bazaar is a beloved community event that takes place every December. The bazaar features local artisans and vendors selling handmade crafts, holiday decorations, and unique gifts.

It’s a festive and fun way to get into the holiday spirit while supporting local businesses.

The event also includes activities for children, such as visits with Santa Claus and holiday-themed games.

Arrive early to beat the crowds and find the perfect holiday gifts for your loved ones.

Try Your Hand at Pottery at The Creativity Cafe Studio

The Creativity Cafe Studio in Woodstock offers pottery classes and workshops for all skill levels. This studio provides a relaxed and welcoming environment where you can explore your creativity.

Participants can create their own pottery pieces, from bowls to sculptures, and take them home as a unique keepsake.

The instructors are experienced and offer personalized guidance to help you bring your artistic visions to life.

It’s a fantastic way to spend a day, especially if you’re interested in trying a new hobby or refining your pottery skills.

Outdoor Adventures at West Thompson Lake

A short drive from Woodstock, West Thompson Lake offers a variety of outdoor activities. The lake is perfect for kayaking, canoeing, and fishing.

There are also many hiking and biking trails in the area, which provide stunning views and opportunities to spot local wildlife.

West Thompson Lake is a versatile destination, ideal for a family outing or a solo adventure.

The area is well-maintained and includes picnic spots where you can relax and enjoy a meal amidst nature.

Home Decor Shopping at The Country Store

The Country Store in Woodstock is a charming shop that offers a wonderful selection of home decor items. From rustic furniture to charming knick-knacks, you’ll find a variety of pieces to beautify your home.

This store is particularly popular for its seasonal decor items, making it a great place to find decorations for holidays and special occasions.

The staff are very friendly and helpful, ensuring a pleasant shopping experience.

It’s a delightful spot to pick up unique items that add a touch of Woodstock charm to your home.

Participate in Seasonal Events at Senexet Grange

The Senexet Grange is a local institution that hosts a variety of seasonal events throughout the year. From craft fairs to community dinners, there is always something happening.

These events are a great way to meet locals and get involved in the community.

One of the most popular events is the annual Harvest Festival, which features live music, homemade food, and activities for all ages.

Attending an event at the Senexet Grange provides a wonderful opportunity to experience the local culture and traditions of Woodstock.

If you’re interested in more local events and activities, you might enjoy exploring some of these highly-rated destinations for unique experiences in nearby areas.

Connect with Nature at Mashamoquet Brook State Park

Just a short distance from Woodstock, Mashamoquet Brook State Park offers a beautiful natural setting for outdoor activities. The park is great for hiking, picnicking, and fishing.

It also features several historical landmarks, including the iconic Table Rock and Wolf Den, which are popular spots for visitors.

Spending the day at Mashamoquet Brook State Park allows you to appreciate the natural beauty of Connecticut and provides a peaceful escape from the daily grind.

The park is well-maintained and offers amenities like picnic tables and grills, making it a convenient spot for a family outing or a relaxing day in nature.

Camping at Salt Rock Campground

Salt Rock Campground offers a fantastic camping experience in the heart of nature. Located near Woodstock, this campground features a range of facilities that make it an ideal spot for both tent and RV camping.

The campground is equipped with amenities like swimming pools, playgrounds, and hiking trails, offering something for everyone.

It is a family-friendly destination where you can enjoy a fun and relaxing camping trip.

Advanced booking is recommended, especially during peak seasons, to secure your spot.

Visit the Putnam Farmers Market

A short drive from Woodstock, the Putnam Farmers Market is another great spot for fresh local produce. Vendors at this market offer a variety of fruits, vegetables, baked goods, and handmade crafts.

The market is open during the warmer months and provides a vibrant atmosphere, making it a fun outing for the entire family.

It is a great place to meet local farmers, learn about sustainable farming practices, and support the local economy.

Be sure to arrive early for the best selection, as some items sell out quickly.

Explore the Quiet Corner Antique Shops

The Quiet Corner, which includes Woodstock and its surrounding areas, is known for its numerous antique shops. These shops offer a wide range of items, from furniture to collectibles, and provide a fascinating glimpse into the past.

The Antiques Marketplace in Putnam is one of the largest antique shops in the area and features a diverse collection of items from various eras.

Exploring these shops is a fun and relaxing way to spend the day, and you might just find a unique treasure to take home.

These antique shops are not only places to shop but also venues to appreciate history and craftsmanship.

Stop by Chase Road Growers

Chase Road Growers is a local favorite for fresh flowers and plants. This family-owned nursery offers a variety of plants, including annuals, perennials, shrubs, and trees.

The friendly staff are always ready to offer gardening advice and help you find the perfect plants for your garden.

In addition to plants, they also sell gardening supplies and decorative items for your outdoor spaces.

It’s a peaceful and inspiring place to visit, especially if you’re looking to enhance your garden with beautiful, healthy plants.

Enjoy a Thematic Meal at the Vanilla Bean Café

The Vanilla Bean Café is not just about food; it’s an experience. This cozy spot frequently hosts themed nights, such as Italian Night or Seafood Extravaganza, offering specially curated menus for each occasion.

Attending one of these themed events can be a fun way to try new dishes and enjoy a unique dining experience.

The atmosphere is always lively, and the staff go out of their way to make each event memorable.

Keep an eye on their schedule so you can plan to attend one of these special nights.

Explore Local Coffee Shops

Woodstock and its surrounding areas are home to a variety of charming coffee shops. Each offers a unique atmosphere and a great selection of coffee and treats.

Sharpe Hill Vineyard Cafe serves delightful pastries and coffee in a cozy setting.

The Grind in nearby Putnam is another popular spot known for its excellent coffee and welcoming vibe.

These coffee shops provide the perfect setting for relaxing with a book, catching up with friends, or simply enjoying a quiet moment alone.

For more options, you can also check out these excellent coffee houses in the region.

Annual Putnam River Fire

For an enchanting evening, head to nearby Putnam for the Annual River Fire event. Held during summer, the River Fire features floating bonfires on the Quinebaug River, creating a magical atmosphere.

The event also includes live music and food vendors, making it a great outing for the family.

It’s a short drive from Woodstock and offers a unique way to experience a summer evening.

Make sure to bring a blanket or chairs and arrive early to find a good spot along the riverbank for the best views.