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

For a peaceful retreat, stay at The Inn at the Roundabout, a beautifully restored 19th-century inn nestled in downtown Simsbury. Located steps from the Simsbury Green, it offers cozy, thoughtfully designed rooms with antique furnishings and modern comforts. Enjoy complimentary breakfast and evening wine hours. Its charming garden courtyard and proximity to local art galleries make it ideal for a serene, culturally rich escape.

The downtown Simsbury area is the prime location for accessing top attractions. Stay near Simsbury Green, where you’ll find the historic Old Town Hall, Simsbury Historical Museum, and seasonal farmers’ markets. Hotels like The Inn at the Roundabout and The Old Mill Inn place you within walking distance of all major sites, offering easy access to local shops, restaurants, and cultural events throughout the year.

While UConn’s main campus is in Storrs, families visiting Simsbury can stay at Courtyard by Marriott Danbury, just 10 minutes away via I-84. It features a kids’ play zone, free breakfast, and an indoor pool—perfect for children. Nearby Hampton Inn Danbury also offers family suites and free shuttle service to nearby shopping centers, making it a practical choice for academic visitors or weekend trips.

Visitors should attend the annual Simsbury Flower Festival, held in spring at the town green, showcasing local horticulture and artisan crafts. Explore the Simsbury Historical Museum to learn about colonial life. In the evenings, relax at The Old Tavern for live folk music or enjoy a coffee at The Roundabout Café, where community spirit thrives. These experiences offer authentic New England charm.

Yes, several hotels in Simsbury provide ADA-compliant accessibility features. Courtyard by Marriott Danbury and Hampton Inn Danbury offer accessible rooms with roll-in showers, grab bars, and wider doorways. The Inn at the Roundabout also features ramps, elevators, and ground-floor accommodations. All properties are certified under the Americans with Disabilities Act, ensuring comfort and safety for all guests.

Nature enthusiasts should explore Huntington Park, featuring 3 km of scenic trails winding through woodlands and along the Huntington River—ideal for family hikes. For more challenging routes, visit the Litchfield Hills Trail Network, which connects multiple ridgelines perfect for autumn foliage viewing. Lookout points offer panoramic views of the Connecticut Valley, while wildlife sightings—including deer and songbirds—are common.

Try locally baked apple pie and artisanal cheese made from pasture-raised milk at Simsbury Farm Stand. At The Roundabout Café, savor traditional New England fare like clam chowder and roast beef sandwiches using farm-fresh ingredients. Don’t miss The Sweet Spot, a neighborhood confectionery famous for handcrafted chocolates—perfect as a souvenir or sweet treat after exploring the town.

Yes, Hampton Inn Danbury and The Inn at the Roundabout welcome pets with no additional fee. Both offer pet beds, bowls, and nearby walking paths. Courtyard by Marriott Danbury also allows small pets upon request. These hotels ensure furry companions feel comfortable, making them ideal for travelers seeking a stress-free trip with their pets.

Most hotels in Simsbury, including Hampton Inn Danbury, Courtyard by Marriott Danbury, and The Inn at the Roundabout, provide complimentary on-site parking. Spaces are secure, well-lit, and accessible 24/7. Some even feature EV charging stations. Parking availability is generous, especially during peak seasons, making it convenient for guests arriving by car.

Simsbury offers a perfect blend of tranquility and culture. With its historic Simsbury Green, charming boutiques, and scenic trails, it's ideal for a low-key weekend retreat. Stay at The Inn at the Roundabout for a nostalgic yet luxurious experience. Enjoy live music, local food, and seasonal festivals—all within a walkable, picturesque New England village setting.