Windsor
Day Trips
Make the most of your day with our curated plans, packed with Windsor's hidden gems and unique experiences!
Start your day with a refreshing walk at Windsor Town Green, enjoying the beautiful landscaping and local art. Grab a coffee at a nearby café to energize yourself for the day ahead.
Visit the Windsor Historical Society to learn about the town's rich heritage. Afterward, have a picnic lunch at one of the local parks.
Enjoy dinner at a local restaurant that serves farm-to-table dishes. Cap off the day with a stroll around the town, taking in the evening lights.
Rent bikes and take a ride along the picturesque Wingo River Trail. The morning is perfect for cycling, with cooler temperatures and gentle sunshine.
Stop at a local brewery for lunch and try some local craft beers. Then continue your bike ride through the scenic vineyards surrounding Windsor.
Return your bikes and unwind at a cozy wine bar, sampling local wines. Enjoy a light dinner at a nearby eatery to wrap up the active day.
Start with breakfast at a trendy café in Old Downtown Windsor. Spend the morning strolling through local boutiques and artisan shops.
Enjoy a leisurely lunch at a bistro and browse some more shops for unique gifts and souvenirs. Don't forget to check out the local farmers' market for fresh produce.
Dine in one of Windsor’s elegant restaurants, indulging in regional cuisine. After dinner, enjoy live music at a nearby venue.
Visit a local vineyard for an early morning tour to learn about winemaking. Enjoy a delightful wine tasting session with breakfast pairings.
Have lunch at the vineyard’s restaurant, savoring dishes made with locally-sourced ingredients. Take a guided tour of several nearby wineries to sample their offerings.
Return to Windsor for a relaxing dinner at a wine country restaurant. Consider joining a wine and cheese pairing experience to enhance your evening.
Start your day with a hike at the nearby Taylor Mountain Regional Park, surrounded by nature. Breathe in the fresh air and take in stunning views.
After your hike, have a picnic lunch at one of the park's scenic spots. Spend the afternoon birdwatching or taking photographs of the beautiful landscape.
Head back to Windsor and enjoy a barbecue dinner at a local grill. Wind down with a walk around the park under the stars.
Visit local galleries to admire art from regional artists. Explore exhibitions and maybe even meet some artists in person.
Enjoy lunch at an artsy café, where the décor is as inspiring as the food. Head to a local theater for a matinee performance.
Dine at a restaurant that features live entertainment. Spend your evening experiencing the performing arts in Windsor.
Visit the nearby Russian River for some early morning kayaking. Enjoy the serene atmosphere and the beauty of the river wildlife.
After returning to shore, refuel with lunch at a riverside café. Spend your afternoon exploring the hiking trails along the river.
Return to Windsor and enjoy an outdoor dinner in a garden setting. Reflect on your day of nature and wildlife exploration.
Begin your culinary adventure with a cooking class at a local farm. Learn to make traditional dishes with fresh, local ingredients.
Enjoy the lunch you've prepared during the class, soaking in the experience. Explore the culinary shops in Windsor for specialty foods and gourmet items.
Dine at a local fine dining restaurant, indulging in a curated menu. Savor wines that perfectly complement each course for an unforgettable culinary experience.
Start at a family-friendly park for some fun morning activities. Organize a game of frisbee or have a playdate with local children at the playground.
Grab lunch at a family diner that has a kids' menu. Head to a local amusement park or arcade for an exciting afternoon.
Enjoy a family-style dinner at a pizzeria. End the day with a movie screening at a local theater, rounding off your family fun.
Start your day with a relaxing morning at the nearby beach or riverbank. Enjoy the tranquility while reading a book or just soaking in the sun.
Have a picnic lunch by the water, making the most of the beautiful scenery. Consider renting paddle boards or canoes for a fun afternoon on the water.
Return to Windsor for a casual dining experience at a riverside restaurant. Enjoy the sunset views while sharing stories from the day.