Westport Connecticut Travel Guide

Nestled on the shoreline of Long Island Sound, Westport, Connecticut is a captivating town brimming with cultural flair, natural beauty, and a calm coastal ambiance. Its blend of artsy sophistication and small-town warmth makes it a compelling destination year-round.

From beach outings and art shows to farm-fresh meals and historic landmarks, Westport offers a memorable travel experience for every kind of visitor. This guide highlights the top places to visit, things to do, and essential tips for making the most of your time in this scenic New England town.

Best Places to Visit

Discover a mix of nature, culture, and history throughout Westport.

• Compo Beach: A lively beach with volleyball courts, a boardwalk, playground, and views of Long Island Sound.
• Westport Country Playhouse: An iconic theater with professional productions and a rich legacy in the performing arts.
• Sherwood Island State Park: Connecticut’s oldest state park with beach access, trails, and sweeping views of the water.
• Westport Farmers’ Market: A seasonal community gathering featuring local produce, baked goods, and handmade crafts.
• Earthplace: A natural science center with wildlife exhibits, educational programs, and nature trails.
• Levitt Pavilion for the Performing Arts: A popular outdoor venue hosting free summer concerts in an open-air setting.
• Westport Museum for History & Culture: Engaging exhibits that tell the story of Westport’s past through preserved artifacts.

Things To Do

There’s something for everyone in Westport, from serene strolls to cultural explorations.

• Relax at Compo Beach: Swim, sunbathe, or enjoy a picnic at this scenic shoreline spot.
• Attend a Play: Catch a live performance at the Westport Country Playhouse.
• Shop Downtown: Explore Main Street’s boutiques, gift shops, and designer outlets.
• Visit Sherwood Island: Take a walk through the park’s trails and stop for birdwatching.
• Explore Local History: Tour the Westport Museum and learn about the town’s colonial roots.
• Go Kayaking on the Saugatuck River: Rent gear locally and enjoy a peaceful paddle.
• Browse Art Exhibits: Check out the Westport Arts Center for rotating art installations.

Where To Stay

Westport offers a variety of places to stay that suit different travel styles.

• Westport Inn: A contemporary hotel offering easy access to downtown.
• Delamar Southport: A luxury boutique hotel located just minutes from Westport.
• The Inn at Longshore: A waterside inn with charming views and romantic ambiance.
• The Westport Hotel: A blend of modern style and coastal charm in a central location.
• Airbnb Rentals: Options range from cozy one-bedroom apartments to full waterfront homes.
• Southport B&Bs: Quaint bed-and-breakfasts in neighboring Southport offer quiet, relaxing stays.

Best Accommodations

Top picks for a comfortable and stylish stay in and around Westport.

• Delamar Southport: Offers upscale rooms, a spa, and fine dining just a short drive from Westport.
• Westport Inn: Budget-friendly with updated amenities and a central location.
• The Westport Hotel: A boutique experience with elegant interiors and excellent hospitality.
• Inn at Longshore: Located along the shore, perfect for weddings and romantic retreats.
• Charming Airbnb Cottages: Private, cozy rentals ideal for families or small groups.

Scenic Road Trips

Westport is a great base for beautiful drives through southwestern Connecticut.

• Merritt Parkway: A tree-lined historic route with unique bridges and scenic views.
• Route 136: Coastal drive through neighboring beach towns and seafood stops.
• Route 1: Takes travelers through picturesque downtowns and antique shops.
• Greens Farms Road: Offers a peek into Westport’s elegant residential neighborhoods.
• Silvermine Arts Center Detour: A scenic ride to nearby New Canaan’s creative haven.

Best Beaches

Enjoy sun, sand, and sea at Westport’s best coastal spots.

• Compo Beach: The town’s main beach featuring wide sandy areas and a family-friendly vibe.
• Sherwood Island State Park: Offers beaches, picnic areas, and walking trails.
• Burying Hill Beach: Smaller and quieter, perfect for tide pooling and sunset watching.
• Southport Beach: A nearby alternative with peaceful surroundings and soft sand.
• Old Mill Beach: A more residential beach offering limited but serene access.

Must-Visit Mountains

Westport is near several beautiful mountainous destinations worth a day trip.

• Bear Mountain: Located in Salisbury with great hiking trails and panoramic views.
• Mount Frissell: Connecticut’s highest elevation point, offering rugged hiking trails.
• Haystack Mountain: Features an observation tower and beginner-friendly trails.
• Sleeping Giant State Park: Known for its mountain shaped like a sleeping giant and varied hiking paths.
• Talcott Mountain: Home to the Heublein Tower and stunning views over the Farmington Valley.

Must-Try Restaurants

Savor the diverse culinary scene of Westport with these popular spots.

• The Whelk: Serves up fresh seafood in a riverside setting with a chic interior.
• Terrain Garden Café: Seasonal dishes served in a lush, garden-themed environment.
• Bartaco: Known for its flavorful tacos and casual, lively atmosphere.
• Kawa Ni: A warm and intimate Japanese-style restaurant with creative small plates.
• Amis Trattoria: Rustic Italian eatery with handmade pasta and hearty dishes.

Best Theme Parks

Add a bit of thrill to your itinerary with a visit to these nearby theme parks.

• Rye Playland: A classic amusement park with historic charm and waterfront rides.
• Lake Compounce: Offers exciting roller coasters and a water park experience.
• Quassy Amusement Park: Lakeside rides and family-friendly activities in Middlebury.
• Adventureland: Long Island’s amusement park filled with rides, games, and food stands.
• Brownstone Adventure Sports Park: A water-focused adventure park with cliff diving and zip lines.

Best Time To Visit

Each season in Westport brings its own appeal.

• Spring (March to May): Ideal for hiking and seeing gardens in bloom.
• Summer (June to August): Great for beach days and local festivals.
• Fall (September to November): Perfect for foliage drives and apple picking.
• Winter (December to February): Quiet months for cozy cafés and indoor arts events.

Transportation Tips

Plan ahead to move easily around Westport.

• Renting a car: Offers the most flexibility for visiting beaches and nearby towns.
• Metro-North Railroad: Connects Westport to New York City and other destinations.
• Uber and Lyft: Readily available for short local trips.
• Taxis: Another option for those not using ride-sharing apps.
• Biking: A scenic way to explore the coast and downtown, with rentals available.
• Walking: Many attractions downtown are accessible by foot.
• Public shuttle services: Limited routes available within Westport.

Things To Know

A few quick facts to help you plan better.

• Weather varies: Bring layers in spring and fall, and warm gear in winter.
• Westport is safe: Exercise basic precautions, especially in crowded areas.
• Reservations are key: Book restaurants and hotels in advance during peak seasons.
• Metro-North is reliable: Makes Westport a convenient day-trip from New York City.

What to Pack

Pack smart for a comfortable and enjoyable stay.

• Layered Clothing: Prepare for cool mornings and warm afternoons, especially in spring and fall.
• Swimwear: Essential for beach visits in summer.
• Rain Jacket: Sudden showers are common, so keep one handy.
• Walking Shoes: Great for exploring the downtown and beach paths.
• Sunscreen and Bug Spray: Useful for park and beach outings.
• Backpack: Handy for day trips and carrying essentials.
• Travel Documents: Keep your ID, hotel info, and rental details organized.
• Camera or Smartphone: To capture beach sunsets and downtown charm.

Facts & Info

• Country: United States
• Capital: Hartford (state capital of Connecticut)
• Largest Metropolitan Area: New York City metro (includes Westport)
• Time Zone: Eastern Standard Time (EST)
• Currency: U.S. Dollar (USD)
• Population: Approximately 28,000
• Airports: Closest major airport is Westchester County Airport (HPN); also accessible via JFK and LaGuardia
• Universities: Nearby institutions include Sacred Heart University and Fairfield University
• Religion: Diverse, with Christian, Jewish, and other faith communities

Estimated Costs

• 3-Star Hotel Room: $150–$250 per night
• 1 Bedroom Apartment Rental: $120–$180 per night
• Rental Car: $40–$80 per day
• Public Transit Ticket: $2–$5 per ride
• Take Out Meal for Two: $25–$40
• Sit Down Dinner for Two: $70–$120
• Draft Beer: $6–$8 per pint

FAQs

• Is Westport walkable?

Yes, especially the downtown area and beaches.

• Can I visit Westport without a car?

Yes, via Metro-North, but a car adds flexibility.

• What is the best time to visit for beach weather?

June through August.

• Are dogs allowed on the beach?

Yes, but usually only during the off-season.

• Is there nightlife in Westport?

The town has casual bars and live music, especially during summer.