Help Check Out Westport’s Terrain

This random request landed in my inbox the other day:

Hi ! I am planning a trip to Westport because of Terrain, and want to find some other unique spots. I have never been to Connecticut. Do you have any must- sees?

Our interests are flea markets, breweries/ wineries, photography, cafes. Any feedback would be appreciated. Thank you much!

This calls for crowd-sourcing. Alert “06880” readers: Help our visitor out. Click “comments” to recommend your must-sees. Explain why, too.

Let’s provide an overwhelming number of choices. I promise to follow up, with a full report on how the visit went.

For photography, I recommend the Westport Arts Center's current exhibit of Lynsey Addario's astonishing shots celebrating Afghan women. Our visitor will find the WAC a fascinating place -- with great photographic opportunities outside too.

For photography, I recommend the Westport Arts Center’s current exhibit of Lynsey Addario’s astonishing shots celebrating Afghan women. Our visitor will find the WAC a fascinating place — with great photographic opportunities outside too.

14 responses to “Help Check Out Westport’s Terrain

  1. 2 roads brewery in Stratford is near Westport and worth the trip.

  2. Bobbie Herman

    There’s a winery at the Hopkins Inn on Lake Waramaug, but it’s about an hour north of Westport.

  3. Well… You have to stay at Longshore!!!

  4. Maureen O'Driscoll

    How about SAC, Stratford Antique Center, full of booths with a variety of nostagia. Also, the flea Market in New Milford is fun, called Elephant’s Trunk or White Elephant (forget the name). Drive up Route 7 for antique and collectible shops! For wine, try Jone’s Tree Farm in Shelton, many local wines and wine tasting, quite fun and picturesque. Believe there is a “Wine Trail” in CT. Woodbury is great area for wines and antiques. When are they coming? Source Westport Chamber of Commerce as well!

  5. After the stop at the Westport Art Center, don’t forget a quick stop at the Westport Historical Society!! Great exhibit about the Westport artists who created so many New Yorker Magazine covers!

  6. Barbara Sherburne '67

    Gouveia Vineyards, 1339 Whirlwind Hill Road, Wallingford. Part of the wine trail.

  7. bobbi essagof

    Don’t miss Westport Pizza!

  8. Mary Ann West

    We always start our first time guests with an introduction tour of Westport, Driving highlights including Earthplace, downtown, Saugatuck, Longshore, Compo Beach, Compo Mill, Sherwood Island State Park and then the gold coast, giving some of the history and stories of the Minuteman statue and current events. In the summer, we include an evening event at the Levitt Pavillion or of course, catch a play at the Westport Country Playhouse.

    Art abounds in Wstpt so try to check out a few, knowing you will want to return. Some just move here, like we did.

    Depending on their food interests we will hit one of our favorite haunts: sometimes its the Black Duck, Mario’s, Mansion or Southport Brewing Company in Southport, Terry Lodge or Tavern on Main, or if they are looking for a “New England” experience, Red Barn, Cobbs Mill in Weston or the table in my kitchen. I know I’ve skipped a great many sites, this is a quick brushstroke of what the Westport area has to offer.

  9. Can’t miss the photo-opportunity at The Cannons. And, is a must.

  10. Maxine Bleiweis

    The Westport Library!

    A fabulous mural by WPA artist Robert Lambdin. Dozens of black and white works on paper by famous Westport artists in the McManus Meeting Room.

    Tintypes of the Erie Canal by NW Gibbons are on display and if they come on Sunday, March 16 at 2, Nate will be driving his vintage truck into the Library to demonstrate how he develops these special prints.

    See a demonstration of 3D printing by inventors of all ages in the makerspace and half-scale GeeBee fighter plane replicas hanging from the ceiling made by Westporters.

    Choose from over 30 programs a week or just come by to relax in a quiet reading room along the Saugatuck River.

  11. Java coffee is my new favorite on Church Lane. Will definitely be a stop on my usual Westport tour for new clients.

  12. Holly Wheeler

    Dan, you’re on a big roll today !!! Lucky us.

  13. Michelle Benner

    Washington Street in South Norwalk (SONO) just down from the aquarium is fun and interesting. There are lots of neat shops including antiques, clothes and home goods, an art gallery, bars and restaurants. The Gingerman has very good pub food and an extensive micro-brewed and international beer & scotch selection. Cafe Rosie in New Canaan is great for brunch / lunch. Delicious food and music, and connected inside to Elm Street books, an independent community bookstore. But most importantly, a drive down to Compo Beach anytime of the day but especially to watch the sunset!

  14. Patsy Cimarosa

    Gilbertie’s, since she’s going to Terrain. Gilbertie’s is way more interesting.