Windsor

Day Trips

Make the most of your day with our curated plans, packed with Windsor's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Start your day with a visit to the Windsor Historical Society, where you can dive into the rich local history through engaging exhibits. Afterward, take a leisurely stroll through the charming downtown area, admiring the beautiful architecture and local boutiques. Don’t forget to grab a coffee from a local café to fuel your morning adventures.

afternoon
:

In the afternoon, enjoy lunch at one of the many eateries in Windsor, sampling local favorites. Afterward, visit the nearby Connecticut River for a scenic walk along the waterfront, taking in the views and fresh air. If you're feeling adventurous, consider renting a kayak or paddleboard to explore the river from a new perspective.

evening
:

As the sun sets, head to a local winery for a tasting experience, where you can learn about the wine-making process and sample some exquisite local wines. Afterward, enjoy a dinner at a cozy restaurant, savoring dishes made from fresh, local ingredients. End your day with a stroll through the historic center, taking in the twinkling lights and vibrant atmosphere.

day 2
Nature and Wildlife Exploration
morning
:

Begin your day at the Windsor Nature Park, where you can enjoy a peaceful hike along the trails surrounded by lush greenery. Bring your binoculars to spot various birds and wildlife that inhabit the area. After your hike, enjoy a picnic breakfast in one of the scenic spots within the park.

afternoon
:

In the afternoon, visit the nearby Northwest Park, which features a nature center and offers interactive exhibits about local flora and fauna. Explore the park's trails or take part in a guided nature walk led by knowledgeable staff. You might even spot some deer or other wildlife as you soak in the beauty of this natural oasis.

evening
:

As evening approaches, return to Windsor and have dinner at a restaurant that offers farm-to-table dishes, celebrating the local harvest. After your meal, unwind at a local brewery, sampling craft beers and enjoying the laid-back atmosphere. Engage with locals and share stories about your day in nature.

day 3
Cultural Arts and Crafts Day
morning
:

Kick off your morning with a visit to the Windsor Art Center, where you can appreciate local art exhibits and perhaps even participate in a workshop. Engage with local artists and learn about their creative processes, which can provide inspiration for your own artistic endeavors. Afterward, explore the surrounding area for unique artisan shops.

afternoon
:

For lunch, head to a café that showcases local artistry in its décor and menu. Post-lunch, join a pottery or painting class at a local studio, where you can unleash your creativity and make a memorable keepsake. This hands-on experience will give you insight into Windsor's vibrant arts scene.

evening
:

As the evening sets in, enjoy a theater performance at a local venue, which often features community talent and professional productions. After the show, grab a light dinner at a nearby bistro, discussing your favorite moments from the performance. Conclude your evening by visiting an art gallery that hosts evening exhibitions or art walks.

day 4
Local Markets and Culinary Delights
morning
:

Start your day at the Windsor Farmers Market, where you can browse fresh produce, artisanal goods, and handmade crafts from local vendors. Engage with the farmers and artisans, learning about their products and the stories behind them. Don’t forget to sample some delicious breakfast treats while you shop.

afternoon
:

After the market, take a cooking class at a local culinary school, where you can learn how to prepare dishes using fresh, local ingredients. Enjoy the fruits of your labor as you share a delicious lunch with fellow participants, celebrating your new culinary skills. Post-lunch, visit a nearby bakery to indulge in some sweet local pastries.

evening
:

For dinner, book a table at a farm-to-table restaurant that emphasizes seasonal ingredients sourced from local farms. Experience a multi-course tasting menu that showcases the best of Windsor’s culinary scene. End your evening with a dessert from a local chocolatier, savoring the flavors of the community.

day 5
Historical Landmarks and Scenic Views
morning
:

Begin your day by visiting the historic Windsor Locks Canal State Park, where you can explore the remains of the canal system that once played a crucial role in the region's trade. Walk along the scenic paths and enjoy the picturesque views of the canal and surrounding landscapes. Take some time to capture the beauty of the area with photographs.

afternoon
:

After your morning exploration, have lunch at a nearby diner known for its classic American fare. In the afternoon, take a guided tour of the Oliver Ellsworth Homestead, a site rich in history related to the founding of Connecticut. Learn about the life of one of the framers of the U.S. Constitution and the significance of the homestead.

evening
:

As night falls, enjoy dinner at a waterfront restaurant, where you can savor fantastic views of the Connecticut River as you dine. Following dinner, take a leisurely walk along the riverside, enjoying the peaceful ambiance and lovely sunset. Consider stopping by a local ice cream shop for a sweet treat to end your day.

day 6
Adventure and Outdoor Fun
morning
:

Start your day with an adrenaline rush at a local adventure park, where you can experience zip-lining, rock climbing, or obstacle courses. The morning air will invigorate you as you tackle the challenges and enjoy the thrill of outdoor adventure. Make sure to take plenty of photos to capture the excitement.

afternoon
:

After working up an appetite, enjoy lunch at a casual eatery that caters to outdoor enthusiasts, offering hearty meals to refuel. Spend the afternoon at a nearby lake, where you can rent paddle boats or canoes for a fun time on the water. Don’t forget to bring a swimsuit if you want to take a dip or relax on the shore.

evening
:

As evening approaches, visit a local park for a community bonfire or outdoor movie night, where you can mingle with locals and enjoy a relaxed atmosphere. Grab some snacks and drinks to enjoy while you watch the film under the stars. Finish your day with a nightcap at a nearby pub, reflecting on your adventurous day.

day 7
Shopping and Relaxation Day
morning
:

Begin your day with a visit to local boutiques and shops in Windsor, exploring unique clothing, gifts, and crafts that showcase the area’s creativity. Take your time to browse through each store, perhaps finding a perfect souvenir to take home. Enjoy a late breakfast at a café that specializes in homemade pastries and artisan coffee.

afternoon
:

After shopping, treat yourself to some relaxation at a local spa, where you can indulge in a massage or facial to unwind after a busy morning. Spend the afternoon enjoying the soothing atmosphere and rejuvenating treatments designed to refresh your body and mind. Afterward, head back downtown for a leisurely lunch at a popular local spot.

evening
:

As the sun begins to set, enjoy dinner at a chic restaurant that offers a comfortable ambiance and a diverse menu. Engage with the friendly staff to learn about the best dishes and local favorites. Conclude your day with a glass of wine at a nearby wine bar, savoring the flavors of the evening.

day 8
Family Fun and Entertainment
morning
:

Kick off your day with a visit to a local amusement center that offers a variety of fun activities for the entire family, including arcade games and mini-golf. Enjoy the lively atmosphere as you compete with family members for the highest scores. Grab a quick breakfast at the center's café to fuel your energy for a day filled with fun.

afternoon
:

After the amusement center, head to a local park that features playgrounds and picnic areas for a family-friendly lunch. Spend the afternoon engaging in outdoor games or simply enjoying the warmth of the sun on a picnic blanket. If time allows, take a family bike ride along the scenic trails surrounding the park.

evening
:

As evening approaches, enjoy a family dinner at a restaurant that caters to all ages, offering a menu full of favorites. After dinner, catch a family-friendly movie at a nearby theater, making it a perfect way to wind down after an exciting day. Finish your evening with some ice cream from a local shop, sharing your favorite moments from the day.

day 9
Visit to Historical Estates and Gardens
morning
:

Start your day with a visit to the historic Wintonbury Hills Golf Course, where you can enjoy the stunning landscape and, if interested, play a round of golf. Take in the beautiful views of the gardens and surrounding areas as you embrace the morning sunshine. Afterward, stop by the estate's café for a light breakfast.

afternoon
:

In the afternoon, explore the nearby Hill-Stead Museum, renowned for its stunning architecture and impressive art collection. Join a guided tour to learn about the history of the estate and its significance in American art and culture. After touring, stroll through the beautiful gardens, admiring the meticulously curated landscape.

evening
:

As the day winds down, enjoy dinner at a nearby fine dining restaurant that offers a seasonal menu inspired by local ingredients. Engage in conversation about the day's experiences and share your favorite moments from the museum visit. End your evening with a nightcap at a cozy lounge, reflecting on the history and beauty of Windsor.

Discover Windsor

Read more in our Windsor 2025 Travel Guide.

Windsor Travel Guide