36 Hours In Westport

Every Sunday, the New York Times fills a page of its Travel section with a “36 Hours in…” feature.

Whether Sonoma County, Mexico City or Boston, the idea is the same:  avoid tourist spots; hit interesting restaurants, galleries and shops; get in, get out, go home.

The Times has never done Westport.  So an “06880” reader suggests we do our own.

“Come up with a Friday night, Saturday all day, and Sunday schedule that yields a maximum amount of enjoyment and gets them from and to a specific Metro North train,” he suggests.

The challenge could include “restaurants, theaters, places for recreation, places to rent vehicles or boats, historically significant places, etc.” The idea is to provide as much exposure to as wide a variety of Westport as possible.

The Times’ 36 hours are tied to the seasons.  So let’s figure out what visitors would like to see and do this fall.  Click the “Comments” link to add your ideas.

Please keep suggestions civil.  The Times does not do snark — and, this once, “06880” won’t either.

A walk by Old Mill -- with a view of the Sherwood Island Mill Pond house -- might interest visitors to Westport.

16 responses to “36 Hours In Westport

  1. Although I haven’t been in quite some time, dinner at The Dressing Room is always a beautiful treat in the fall. I love the entrance with all the fall trees when you drive in, but the front dining area with the fireplace makes it very cozy and the food is delicious! Westport in the autumn for me is always about the simple things, though. I just love to walk downtown and smell fall, feel the crisp air on my face and window shop. It’s also my favorite time at the beach. Sadly, my dog passed this year, but from October 1st they are allowed at the beach and it’s wonderful. Westport is beautiful year round, it just so happens the fall/winter time in Westport is my favorite. I look forward to reading other comments and maybe learning something new about Westport. I’ve been here since 1971, but I still think there area hidden treasures! Have a wonderful day. Thank you, Dan, for this wonderful treat!

  2. Innocent Bystander

    Get the 7:37 p.m. Friday night from Grand Central to Saugatuck station. Head straight to the bar at Mario’s and have a prime rib dinner following your prerequisite number of drinks needed after living in Manhattan for the week. Stay the night at the Longshore Inn. Get a 8:32 tee time at Longshore Golf Course for a round of 18 holes followed by lunch at Splash. Prearrange bikes for a ride after a lengthly nap after living in Manhatan for the week and stroll around the beach. After a second nap, take a cab out to Rowayton Seafood for dinner, returning to the Longshore Inn for the night. On Sunday, run in the preregistered Westport Road Race Five Miler with a cool down game of tennis at Longshore following. Once again, lunch at Splash with the muscles in claim sauce. Take another nap followed by another bike ride downtown to see the variety of store fronts outlets you already have in Manhattan and stop by for the matinee at the Westport Playhouse. Return bike and cab should allow you to get the 6:08 p.m. train out of Greens Farms in time to return to Manhattan and take a nap in preparation of another week living in Manhattan. Cost: $912.38 Experience: Priceless

    • Richard Lawrence Stein

      Innocent….. first of all you went off the reservation on going to Rowayton…. it was suppose to be Westport and its gems not Norwalks…..secondly unless the Inn has some kind of deal for the guests…only local pass carrying or guests of pass carrying and playing with can get onto longshore to play golf….

      • The Innocent Bystander

        Bad me. But only you would point it out. RS is worth going off the “reservation” compared with most of the dumps you suggested and I believe you can get a tee time on a weekend for a non-resident if you stay at the Inn.

        • Longshore non-resident policy

          Longshore Club Park is now available to non-residents. Non-residents may book tee times for play Monday – Thursday up to two days in advance starting at 7:30 a.m. at (203) 341-1833 or online at http://www.longshoregolf.com

          Friday, Saturday, Sunday and Holiday play for non-residents is on a walk-up basis only.

        • Richard Lawrence Stein

          Thanks for the clarification Jeff, but Innocent I was following the rules and find Rowayton to be crowded and uninteresting plus I would call none of those places a dump except The Duck which is a cherished and dear place

          • The Innocent Bystander

            Duneville’s? Ug! Pete Atkins at Black Duck is a former classmate and I should have given him a plug. Your description was nice. Jeffxs: Thanks for the clarification but I did, indeed, say “tee time” and I believe that is available for non-residents who stay at the Inn, seven days a week.

  3. Wow, Innocent Bystander, that’s impressive!!! !! :)) Well done!!!

  4. Looking forward to those “muscles in claim sauce” at Splash.

  5. Challenge: Can anyone come up with a weekend in Westport plan for an individual or couple who, say, live on Social Security or some other form of fixed income? Just sayin’.

  6. Innocent Bystander

    Take the 7:23 p.m. bus from Port Authority to Stamford and take the local train to Greens Farms. Walk up to the Westport Inn and ask for the AARP rate on a single room. Awaken to their breakfast buffet and sneak enough food back to the room for lunch. Hoof back to Greens Farms beach area and take a walk down to Southport Beach taking in the sights of Imus’ house and Phil and Marlo’s estate. Lob out on the beach with plenty of sun screen and take a nap. Hitch hike back to the Westport Inn and have lunch from the breakfast buffet. Take a nap after your mid-day regiment of pills. After the nap, walk over Blockbuster and get a recent release or perhaps “The Man in Grey Flannel Suit” would be appropriate. Keep walking down to the Chinese take-out on the Post Road and return to the motel to watch a movie, shrimp fried rice and take your nightly regiment of pills. A midnight swim in the pool would be fun after you fall asleep during the movie. Up bright and early the next morning for a second run at the breakfast buffet and stash enough of their fruit and bagels for lunch. Take the meto bus downtown and browse around the corporate shops and a walk around Winslow Park. This should leave plenty of time to attend the 11:00 church service at Saugatuck Congregational Church followed by a stroll down to see the cemeteries on Evergreen Parkway. Another walk up to the Westport Playhouse to try and catch a glimpse of the actors performing the matinee and split a meatloaf sandwich at the Dressing Room. Pictures taken in front with Robert Redford who just happens to be having lunch there as well. Return bus to Westport Inn for a quick nap before checking out and after the afternoon regiment of pills. Walk down to the beach for a leisure swim at the beach before getting the 5:38 p.m. train back to Grand Central while you nibble on the fruit and bagel you got at the breakfast buffet.
    Price: $348.63 Experience: Probably should have gone to the U.S. Open

  7. Westporter since 1970


    Arrive early and get a Westport taxi to catch a Staples soccer game at Wakeman or Loeffler field, one of the highest elevations in Westport. Whether varsity or JV you will experience a spirited game by frequently county and state contenders. 2:45 is kickoff.

    Or arrive later and check out the shops and restaurants on Railroad Place. Catch a Westport taxi to the Longshore Inn where you’ll stay for two nights. Check out the golf course and tennis courts, walk around the charming Strait marina. Depending on weather and your inclination, arrange for a tee time, tennis court or sailboat rental at the Longshore Sailing School on the grounds. Either have cocktails and dinner at Splash or get back to Railroad place for drinks and dinner at Mario’s, a Westport classic.


    Many choices: If you’re not golfing, playing tennis or sailing at Longshore, rent bikes from Cycle Dynamics on the Post Road. Biking takes courage in Westport traffic but it’s a great way to get from ATM to ATM in this charming bank-filled town.

    Cruise the Main Street shops down to the Westport Public Library for a nice river view and free wifi or connect with a colorfully clad group of bikers and head out on the country or shore-side roads. You’ll see some very expensive automobiles that only get driven on Saturday mornings. Try Doc’s on Riverside for coffee and a pastry or Coffee ‘An further up on Main St. for a great non-franchised coffee and breakfast.

    2PM Saturday. Most Saturdays in October, you can make your way to Staples High School for premier schoolboy football. Staples championship team always provides a thrill, and there are three Saturday games in October. Check the team’s website for the admission price.

    Dinner at Le Farm… get early reservations and choose the smaller portions. Mention that you’re heading to the Westport Playhouse (across the Post Rd), and they’ll time your dinner appropriately

    8PM Tap into Westport’s deep theatrical roots by taking in “The diary of Anne Frank” at The Westport Playhouse. Enjoy the refurbished and rejuvenated theater. This is where Richard Rodgers was inspired to get the rights to “Green Grow the Lilacs” which he and Hammerstein transformed into “Oklahoma.”

    (If you’re considering a move to Westport, and schools are what you’re looking at, time your visit so you can catch a Staples Player production… you’ll see professional level theater on Nov 14.)


    Walk or bike to Old Mill Beach then along the shore to Compo Beach. The religiously and socially inclined find a number of sunrise services near the cannons at the end of the beach. Or bring your iPod touch; there’s free wifi at the beach, too. (Why do you need Wifi? Keep up with the daily refreshed “06880” http://06880danwoog.com/)

    At 10 AM go to the Farmer’s Market. The big Westport farmers’ market is on Thursday, but there is a terrific small one tucked behind the historic Saugatuck Congregational Church. Buy a fall pumpkin from Belta Farms—the only remaining farm in Westport or apples from Gazy’s a picturesque farm stand cum truck.

    Walk over the The Dressing Room for brunch. It’s a locavore restaurant started by longtime Westporter Paul Newman. No more walking; you’ll need Westport Taxi to get you back to the station..

    • Great ideas, Westporter Since 1970 — and thanks for the Staples soccer shout-out. Unfortunately we have no Friday afternoon regular season home matches — but we welcome anyone any time at our training sessions, right after school.

      For everything Staples boys soccer-related, check out http://www.StaplesSoccer.com — see you on The Hill!

  8. • Book two nights in a private Westport home for only $70 a night

    • Friday night dinner: Mansion Clam House
    • Night cap: Margarita at Viva Zapta

    •Saturday breakfast: Oscar’s Deli on Main Street
    Lunch: Blue Lemon Restaurant
    Catch afternoon matinee at the Playhouse
    Dinner: Bobby Q’s

    •Sunday breakfast: Sherwood Diner
    Lunch: Bogey’s Grille & Tap Room
    People-watch at the Compo
    Dinner: Nistico’s The Red Barn

  9. Richard Lawrence Stein

    With all things considered and weather not an issue…..Take the 5pm train out of GC…arrive in our fair town at just after 6pm….. Go to Mario’s for a quick cocktail to unwind…. but head over to the Legendary Black Duck for some great food and local lore, plus it has the claim to fame of being on the FOOD NETWORK….get a good dose of the local people and their watering hole… plus they have bands most weekends…. get a taxi and head over to the Inn at Longshore for a Night cap at Splash….. ask for the hotel to arrange a car…so you can get about….. Saturday morning head out for a nice walk of the Longshore/Compo/Old Mill area….get a little something at Elviras and pick up a morning paper…head into the Old Mill Beach Area and walk to the Old Mill Locks and take in the beauty of the pond and views..what a perspective…. sit at the beach there or back at Compo and just take it easy….after that… Joey’s at Compo should be open, maybe get a snack and head back to go out for a lunch in Westport…. I would suggest either…. Tavern on Main….The River Tavern…. Oscars….. or Bogey’s…all are good and offer variety in both dollars and menu…. then walk around town…explore explore explore….. Go to the Westport Historical Society…I bet you could get some great perspective on the town and maybe an interesting tour of it by some very friendly people there…..also try the Westport Nature Center/Earth Place for a fun woodsy walk….in the later pm relax a bit and head back to the Inn…. Saturday Night take in a dinner to die for at Le Farm….DaPietro…..or maybe at the Saugatuck Rowing Club…. all very good and a showcase to the BEST in Westport fare…. finish the evening with some energy and see any number of bands in the Saugatuck bar scene… Sleep a bit in on Sunday…..have brunch at Duneville’s, Bogey’s, or Coffee’an (the best donuts ever!!!)… take in the Westport Art Center…. and then go for a car ride through the coast and then up into the woods….see the rest of Westport and its various areas…..head to the station and wave good-bye……

  10. Looking for a wonderful summer fun spot come to Westport! If you like to know a bit about our famous residents, dine at Paul Newman’s Dressing Room and visit he Westport Country Playhouse. For a fun daytime activity head out to Longshore Sailing School (you can park without a town decal in the gravel lot just a little further away) and rent kayaks or sailboats… or come back regularly and sign up for regular lessons at the sailing school! Take a walk from Long Shore, to Compo Beach via the marina, and then walk along the beach /sidewalk all the way to Elvira’s before heading back. You’ll get a great feel of Westport and enjoy the beach and salty smell of the ocean (OK – I know it’s the Long Island Sound – but let’s not get technical). To finish off the summer feel, head to Splash back at Longshore (near your parked car) where you can order lobster dinner in a great environment.