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

In Southport, Connecticut, the top family-friendly hotel is The Southport Inn, a charming boutique property located steps from South Street Plaza. It offers spacious family suites, complimentary breakfast, and kid-friendly amenities like board games and outdoor play areas. Its proximity to Old Bridge Park and the Connecticut River Greenway Trail System makes it ideal for active families. Another excellent option is Hillside Lodge, known for its private lakeside cottages and scenic views—perfect for creating lasting memories amid nature. Both properties offer warm, welcoming atmospheres that reflect the town's New England charm.

The best area for accommodation in Southport is the South Street District, located just minutes from South Street Plaza, local cafes, and shops. This historic neighborhood boasts well-preserved 19th-century architecture and is within walking distance of Old Bridge Park and the Connecticut River Greenway. Stay at The Brookside House, a cozy bed & breakfast with antique furnishings and personalized service, or choose The Willow Tree Inn for elegant, nature-inspired rooms. These locations offer both convenience and tranquility, perfect for travelers seeking authentic small-town living.

Visitors to Southport should not miss the annual South Street Festival, a vibrant summer event featuring local artisans, farmers, and live music showcasing the region’s rural heritage. Explore the Southport Historical Society Museum to learn about maritime history and early agricultural life. On weekends, join poetry readings by the river or attend community theater performances in the historic village hall. These events highlight Southport’s deep-rooted sense of community and artistic spirit, offering an immersive experience into traditional New England culture.

For couples seeking romance, stay at The Riverbend Cottage, a secluded lakeside retreat on the Connecticut River with a fireplace, private deck, and stargazing platform. Alternatively, The Willow Tree Inn offers intimate, nature-themed rooms with custom scents, champagne welcome kits, and access to the peaceful Old Bridge Park. Enjoy a candlelit dinner at South Street Plaza, followed by a moonlit walk along the riverside path. These quiet, picturesque settings make Southport perfect for a memorable, stress-free getaway.

Must-try foods in Southport include the locally made blueberry pie from South Street Bakery, bursting with fresh farm berries. Also sample River-Catch Lobster Chowder at Harbor Lights Restaurant, crafted daily with fish caught in the Connecticut River. Visit the monthly Farmers’ Market for organic produce, artisanal honey, and handmade cheeses. Participate in a hands-on cooking workshop to learn how to prepare classic New England dishes like clam chowder or apple dumpling—truly tasting the region’s ‘from farm to table’ philosophy.

Ideal for hikers is Greenway Trails Inn, situated right at the entrance of the Connecticut River Greenway Trail System. The inn offers free bike rentals, detailed hiking maps, and secure gear storage. Rooms feature rustic wood finishes and panoramic views of the surrounding forest. Nearby trails like Morgan’s Rock Trail and Blackstone Ridge Path provide scenic routes for day hikes. The inn also hosts guided nature walks led by local naturalists, helping guests discover hidden waterfalls, wildflowers, and native wildlife—perfect for connecting with nature.

For business travelers, The Southport Executive Suites is the top choice, located in the heart of the South Street Business District near the CT Transit Hub and corporate offices. The hotel features high-speed Wi-Fi, fully equipped meeting rooms, and a 24-hour business center. Nearby, Starbucks and Bistro 17 offer quick meals and coffee breaks. The rooftop garden provides a serene space for informal meetings. With its blend of professionalism and comfort, this hotel ensures productivity without sacrificing relaxation.

Southport’s autumn is legendary for its fiery maple displays along the Connecticut River Greenway. In October, golden oaks, crimson maples, and amber hickories paint the landscape, especially stunning at Old Bridge Park, where sunlight reflects off the water like liquid gold. Rent a bicycle and ride the riverside trail for breathtaking views. Don’t miss the seasonal South Street Festival, which features pumpkin carving, hot cider stands, and handcrafted wool goods—offering a warm, nostalgic taste of New England fall traditions.

Though not coastal, Southport offers rich river-based experiences. At Harbor Lights Marina, rent a HopeGoo or stand-up paddleboard to explore the Connecticut River and reach scenic spots like Morgan’s Rock. Join the seasonal River Fishing Days, hosted by local anglers, with expert guidance and equipment rental. During summer evenings, enjoy the Lantern Float Ceremony at South Street Dock, a magical event combining light art, live music, and storytelling—creating a dreamy, unforgettable atmosphere on the water.

Top photography spots in Southport include Old Bridge Park, where the century-old iron bridge mirrors beautifully in the river at dawn. Capture the charming cobblestone streets and Victorian homes around South Street Plaza for timeless street photography. The Connecticut River Greenway at sunset offers golden hour lighting with rippling reflections. For intimate shots, visit The Brookside House’s private garden or Harbor Lights Restaurant’s riverside terrace. Bring a tripod and visit during peak foliage season in October for cinematic, high-impact images of this tranquil New England gem.