Windsor(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

For a peaceful retreat in Windsor, Connecticut, consider staying in the Riverfront District or near Windsor Green. The Windsor Inn offers charming accommodations with views of the Hudson River, perfect for those seeking tranquility and historic ambiance.

Alternatively, Hartford Country Club Lodge provides a secluded escape within a scenic golf course setting, ideal for nature lovers and those wanting a serene countryside experience. For an authentic local touch, book a stay at Willow Creek Farmstay, a rustic-chic farm guesthouse where guests can participate in seasonal harvests, artisan workshops, and farm-to-table dining—offering deep immersion into Connecticut’s rural heritage.

Yes, Windsor Family Resort & Spa is ideal for families seeking outdoor fun. It features an indoor children’s pool, mini-golf course, supervised playrooms, and hands-on cooking classes for kids.

Located steps from Windsor Park, the resort offers easy access to lakeside trails, picnic areas, and seasonal events like outdoor movie nights. For a more immersive experience, Willow Creek Farmstay hosts animal feeding sessions, pottery workshops, and stargazing evenings—all set on a working farm. Families can also camp in designated tent sites with guided nature walks, making it a top choice for active, nature-connected vacations.

The heart of cultural and historical exploration in Windsor, CT lies in the Windsor Town Center. This area houses the Windsor Historical Society Museum, the centuries-old St. John's Church, and restored colonial-era homes now serving as art galleries and independent bookshops.

Each spring, the Windsor Heritage Festival transforms the town into a living museum, featuring horse-drawn carriage parades, period costumes, and colonial craft booths. Strolling along the cobblestone paths surrounding Windsor Green, visitors can admire well-preserved 18th-century architecture. Stay at the Old Town Inn, a 1790 farmhouse-turned-hotel, which offers daily guided walking tours uncovering hidden stories behind local landmarks and early American life.

A must-try culinary experience in Windsor, Connecticut is visiting the Windsor Farmers Market every Sunday morning, where vendors offer freshly baked apple pie, local honey, and small-batch maple syrup straight from nearby farms.

Dine at Hearth & Vine Restaurant, a Michelin-recognized eatery that champions ‘farm-to-table’ cuisine using seasonal ingredients sourced from regional producers. Signature dishes include wild venison with blackberry reduction and slow-roasted carrot tart.

For a hands-on experience, book a Farm Kitchen Workshop at Willow Creek Farmstay, where guests harvest vegetables, prepare a traditional American barbecue, and enjoy a meal cooked over an open fire—perfect for food lovers craving authenticity.

For intimate weddings and romantic honeymoons in Windsor, CT, Old Town Inn stands out with its 18th-century architecture and private courtyard, accommodating up to 30 guests for outdoor ceremonies paired with candlelit dinners and live piano music.

Riverbend Estate, a secluded lakeside manor, features a glass-walled wedding pavilion, private dock, and panoramic views of the Hudson River. Its honeymoon suite includes a spa bathtub and floor-to-ceiling windows overlooking the water.

For a nature-inspired celebration, Willow Creek Farmstay offers “Forest Wedding Packages,” allowing couples to exchange vows beneath trees, followed by a rustic picnic reception in a barn-style event space—ideal for couples seeking an authentic, earthy romance.

In Windsor, Connecticut, the Windsor Green Trail is a 2-kilometer loop through ancient oak forests, offering excellent wildlife spotting opportunities with sightings of squirrels, blue jays, and woodpeckers—ideal for family hikes.

For longer adventures, the Hudson River Trail stretches 6 kilometers along the riverbank, featuring scenic overlooks, fishing platforms, and stunning sunrise views across the water—perfect for photographers and nature enthusiasts.

The Windsor Wetlands Preserve provides guided boat tours through reed beds and marshes, where visitors can observe migratory birds, herons, and beavers. Educational programs on wetland conservation make it a standout destination for eco-conscious travelers seeking immersive natural experiences.