What to do and see in Westport, United States: The Best Places and Tips

October 11, 2017 Diedre Savory

Westport is an affluent town located in Connecticut, along Long Island Sound within Connecticut's Gold Coast in Fairfield County, Connecticut. It is 29 miles (47 km) northeast of New York City. The town had a population of 26,391 according to the 2010 U.S. Census, and is ranked 22nd among America’s 100 Richest Places as well as second in Connecticut, with populations between 20,000 and 65,000.
Restaurants in Westport

1. Westport Country Playhouse

25 Powers Ct, Westport, CT 06880-3621 +1 203-227-4177
Excellent
70%
Good
26%
Satisfactory
3%
Poor
1%
Terrible
0%
Overall Ratings

4.5 based on 130 reviews

Westport Country Playhouse

Reimagining itself in recent years, Westport Country Playhouse is rapidly emerging as a nationally recognized professional theater. Under the artistic direction of Mark Lamos and management direction of Michael Ross, the Playhouse creates five live theater experiences, produced at the highest level, from April through November. Its vital mix of works---dramatic, comedic, occasionally exploratory and unusual---expands the audience’s sense of what theater can be. The depth and scope of its productions display the foremost theatrical literature from the past---recent as well as distant---in addition to musicals and premieres of new plays. During the summer, the Playhouse is home to the Woodward Internship Program, renowned for the training of aspiring theater professionals. Winter at the Playhouse, from November through March, offers events outside of the main season---Family Festivities presentations, Script in Hand play readings and a Holiday Festival. In addition, businesses and organizations are encouraged to rent the handsome facility for their meetings, receptions and fundraisers

Reviewed By Joe1234665 - Weston, Connecticut

The playhouse did a season ending musical, Camelot and did it very well.

It is a challenge to get a full production musical on the small stage and with a cast large enough to look convincing. Westport county Playhouse pulled it off.

Slick scenery, a small but capable staff and you have a good evening of enjoyment.

I hope they do more musicals

2. Sheffield Island Lighthouse

4 N Water St, Seaport Dock, Norwalk, CT 06854-2228 +1 203-838-9444
Excellent
73%
Good
22%
Satisfactory
3%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 249 reviews

Sheffield Island Lighthouse

The Norwalk Seaport Association has owned, restored and maintained Sheffield Island Lighthouse since 1986 and is the official U.S. Fish & Wildlife Service Friends group for the Norwalk Islands.Sheffield Island with its historic 145-year-old lighthouse, beaches and wildlife refuge offers abundant summer fun for visitors. From May through September, visitors can board the Seaport Association's 45-foot C.J. Toth catamaran for a cruise to the island then tour the lighthouse, observe wildlife in their natural habitat in the Stewart B. McKinney National Wildlife Refuge, hunt for shells along the beach, dine on a picnic lunch, play on the lawns around the lighthouse and just have a good time. The lighthouse tower provides magnificent views of Long Island Sound and, on a clear day, of the New York City skyline. Join us for one of the most exciting tours that the Norwalk Harbor Islands area has to offer! During this unforgettable adventure tour of Sheffield Island and Lighthouse, you'll step directly from the boat into the past.

Reviewed By josephcG8864QA - Versailles, Missouri

We didn't realize you needed advance tickets but fortunately two seats opened up and my wife and I were able too go. Dan, the tour guide, was very knowledgeable about the area and was a terrific guide to the lighthouse itself. All three, Dan, the first mate, Andy, and the captain were all very professional.

3. The Philip Johnson Glass House

199 Elm St, New Canaan, CT 06840-5321 +1 203-594-9884
Excellent
82%
Good
15%
Satisfactory
1%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 158 reviews

The Philip Johnson Glass House

Reviewed By jdms33 - Monroe, Connecticut

Finally made the trip and so glad we did. The property and facilities are just stunning. We did a self guided tour and really enjoyed it. The docents are all very knowledgeable and there was someone at every location ready to answer questions and/or share their knowledge of the property and people associated with it.

My favorite building on the property was the sculpture building...less about the collection, although it was nice, but much more for the architecture of the building and the lighting through the glass roof.

My least favorite was the painting gallery.

The glass house itself is absolutely unique and while it is consistently referred to as the crown jewel of the property I found a number of the other buildings much more interesting as well as the stories about the grounds....which all look very natural but apparently are as well thought out as the structures on the property.

4. Compo Beach

60 Compo Beach Rd, Westport, CT 06880-6853 (203) 341-5090
Excellent
57%
Good
30%
Satisfactory
11%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 159 reviews

Compo Beach

Reviewed By Hans_Sachs - Southport, Connecticut

Lobsterfest is an event organized by the Westport Rotary Club, once a year. It's held on Compo Beach. This year's event was today, on September 16.
It's a family-friendly, traditional New England clambake, based around a very generous lobster dinner (two decent-sized lobsters per person, plus all the trimmings). Wine and beer is included in the price, and there is a raw bar where you can buy fresh oysters and shrimps.
They have live music. While we were there this year(this afternoon), the band played Grateful Dead numbers, which was fine.
The Weather Gods co-operated this year, but the tables are sheltered under tents, so don't be deterred if the weather turns nasty. We were here a few years ago, when it was cold and rainy, but it didn't make a lot of difference.
Oh yes, and Compo Beach is normally out of bounds for non-residents at this time of year, but that doesn't apply to people who attend Lobsterfest.
You've missed this year, but try next year, if you get a chance.
Recommended.

5. The Maritime Aquarium

10 N Water St, Sono District, Norwalk, CT 06854-2228 +1 203-852-0700
Excellent
58%
Good
31%
Satisfactory
9%
Poor
1%
Terrible
1%
Overall Ratings

4.5 based on 893 reviews

The Maritime Aquarium

Awarded the 2013 Certificate of Excellence by Trip Advisor. The Maritime Aquarium inspires people of all ages to appreciate Long Island Sound and protect it for future generations.

Reviewed By avstrait - Stamford, Connecticut

We are Patrons of the Norwalk Maritime Aquarium BUT we are very unhappy that the fact that Long Island Sound is dying or dead depending on where you go in Fairfield County. As a child l could walk along any beach in Greenwich, Stamford, or Darien and find all kinds of sea life: minnows, crabs, snails, Starfish, hermit crabs, clams, mussels, etc. etc. Today if you walk along those same beaches you find NOTHING!! Thirty or more years ago you could fill a bushel basket with fish you caught to take home within an hour (flounders, sea bass, blowfish, blackfish, weakfish, etc.) Today you would be lucky to catch anything and the only fish that come into the sound are migrating fish who only come for a short time, like stripers, menhadden/bunker, or bluefish. The Maritime management should be educating the Public that SO;METHING SHOULD BE DONE ABOUT THIS AND THEY SHOULD NOT BE IGNORING THIS! The displays throughtout the Norwalk Maritime Aquarium at present would give you the idea that all is well with Long Island Sound.

6. Stepping Stones Museum for Children

303 West Ave, Mathews Park, Norwalk, CT 06850-4002 +1 203-899-0606
Excellent
58%
Good
27%
Satisfactory
10%
Poor
4%
Terrible
1%
Overall Ratings

4.5 based on 224 reviews

Stepping Stones Museum for Children

Stepping Stones Museum for Children ignites a child's love of learning through play. Open your world to our hands-on exhibits and exciting programs. With our five main galleries and over 100 hands-on activities, children become wide-eyed with wonder. As they see, hear, touch, feel and do, their ever-growing minds venture to amazing new places. Our Traveling Exhibit Gallery changes every few months so you can always expect new and fascinating adventures. Stepping Stones mission is to broaden and enrich the educational opportunities for children ages ten and under and to enhance their understanding of the world. The museum seeks to create an environment that inspires lifelong learning and supports parents, caregivers and educators as facilitators of children's explorations. Stepping Stones is open daily between Memorial Day and Labor Day, and CLOSED Mondays between Labor Day and Memorial Day (School Year Hours) Hours are 10:00 am - 5:00 pm.

Reviewed By FrankRod89 - Norwalk, Connecticut

Kids love this place! It’s got everything for them to stay busy and have an awesome time. Very interactive for the kids with lots of activities and games for them to play. Also learning while playing. Big outdoor playground with blocks for them to build up and other toys.

7. Fairfield Cheese Company

2090 Post Rd, Fairfield, CT 06824-5674 +1 203-292-8194
Excellent
82%
Good
18%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 38 reviews

Fairfield Cheese Company

Reviewed By Chris C - Fairfield, Connecticut

It is so nice to have a wonderful cheese shop in the area with knowledgeable owners and staff. I hope to be able to make it to more of the tastings this fall.

8. Sherwood Island State Park

Sherwood Island Connector, Westport, CT 06880 +1 203-226-6983
Excellent
37%
Good
46%
Satisfactory
10%
Poor
5%
Terrible
2%
Overall Ratings

4 based on 140 reviews

Sherwood Island State Park

Reviewed By CGin23 - New Jersey

We drove to Sherwood Island State Park for Chowdafest. It is a pretty scenic drive through the Hudson River Valley from NJ. When we arrived at the park we had the view of a beautiful, long, sandy beach. The beach was clean and there were large clean bathrooms and a path to walk along the beach as well. We will be back to visit in the summer.

9. Earthplace

10 Woodside Ln, Westport, CT 06880-2322 +1 203-227-7253
Excellent
64%
Good
33%
Satisfactory
3%
Poor
0%
Terrible
0%
Overall Ratings

4.5 based on 30 reviews

Earthplace

Reviewed By nytraveller2020 - New York City, New York

This is an exceptional nature center with educational and just fun exhibits for all ages. The surrounding property is laced with hiking trails, through woods and fields, and near streams. The trails are mostly easy walking for young and old, and the scenery is beautiful.

10. Lockwood-Mathews Mansion Museum

295 West Ave, Mathews Park, Norwalk, CT 06850-4002 +1 203-838-9799
Excellent
58%
Good
34%
Satisfactory
4%
Poor
2%
Terrible
2%
Overall Ratings

4.5 based on 75 reviews

Lockwood-Mathews Mansion Museum

The Lockwood-Mathews Mansion Museum is regarded as one of the earliest and finest surviving Second Empire Style country houses ever built in the United States. The 62-room mansion was built by banker-railroad tycoon LeGrand Lockwood, who in 1864 began construction of his estate on the Norwalk River in Norwalk, Connecticut. Designed by European-trained, New York-based architect Detlef Lienau, the mansion, which was completed in 1868 at a cost of over $2,000,000.00 in 1868 currency, is considered his most significant surviving work. American craftsmen, along with many immigrant artisans, were employed in the construction of the house. Following Mr. Lockwood's financial reversal in 1869 and his untimely death in 1872, his wife, Ann Louisa Benedict Lockwood, lost the house in foreclosure to the Lake Shore & Michigan Southern Railroad in 1874. At the time, Mrs. Lockwood owed one remaining mortgage payment of $90,000 - Mr. Lockwood had paid off $310,000 of his mortgage which he took out following the tragic financial disaster of Black Friday in 1869. After remaining unoccupied for two years, the mansion was purchased in 1876 by Charles Drelincourt Mathews, a wealthy provisions merchant who retired at an early age. The purchase price from the Lake Shore & Michigan Southern Railroad astonished many. The house, not even a decade old, along with its numerous outbuildings within the 30-acre compound, was sold for a fraction of its value: $90,000.00 - the last payment owed by Mrs. Lockwood. However, much work had to be done in order to occupy the now unfurnished mansion and the grounds, never completed, were commissioned to Fredrick Law Olmstead. Charles and Rebecca had 4 children: Lillie, Florence, Charles Thompson, and Harold. Lillie and Harold both married, had children, and summered at the Mansion; Florence and Charles never married and lived at their townhouse at 812 Fifth Avenue in NYC in the winter or when not traveling throughout Europe. Charles Thompson Mathews, a world-renowned scholar in the field of architecture, won an international competition for the design and construction of the Lady Chapel at St. Patrick's Cathedral in NYC in 1899. His two books on the subject were used as textbooks at Ivy League schools such as Columbia, Harvard, and Yale. Following his death in 1934, Miss Florence Mathews made Norwalk her full-time residence and passed away in her father's mansion in 1938. The house was first leased and subsequently sold to the City of Norwalk for "park purposes." Years of neglect along with use by City Offices and storage of heavy machinery severely deteriorated the once beautiful home. When the City announced their plans for demolition in the early 1960s in order to build a new City Hall near the mansion, 16 taxpayers, later incorporated into "The Common Interest Group", sued the City of Norwalk and following a lengthy court battle, the Mansion was saved in 1965. In 1971, the Mansion was officially declared a National Historic Landmark. Today, the Museum is being lovingly restored back to its original grandeur by a non-profit organization and is a cultural gem which highlights the lives, styles and technology of the Victorian Era. Tours are offered early April through early January, Wednesday-Sunday. Tours are conducted on the hour at 12, 1, 2, and 3 p.m. Admission: $10 Adults, $8 Seniors, $6 Students 8-18, and Free for Children under the age of 8.

Reviewed By CharismaJ2 - Melbourne, Florida

We took the "Witches, Vampires, and Ghost Tours at the Mansion," an event that happens in October. Held at night and you're given small battery-operated candles, walking through the dimly-lit mansion and hearing the ghostly tales, it is FANTASTIC!!! They take small groups at a time. You don't hear or get to see much about the history of the mansion itself, so be sure to come back during the day for that tour. I love Halloween, so this was a treat for me!! This mansion was used for some scenes in "The House of Dark Shadows" which was a 1970 film based on the television series.

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