ITINERARY: 2-3 Day Kosher Road Trip to Southern CT

Last summer, my family and I enjoyed a 2-day road trip through Southern Connecticut over the July 4th Independence Day weekend. For those in the Tri-State or New England regions, Southern CT is a great place to visit or vacation with lots of beaches, a calm-watered coastline on the Long Island Sound, and a growing number of kosher restaurants and establishments peppered throughout the region.

This is a great short family-friendly trip that can be enjoyed over 2 days/1 night or 3 days/2 nights depending on your schedule, and easily over a Sunday + Monday when Monday is a holiday weekend (eg. Memorial Day or Labor Day weekends), especially those living near NYC or Boston.

The following itinerary starts from the NYC area and can be customized and altered depending on your starting point.

Links to all restaurant menus mentioned can be found at the end of this article.

DAY 1: After having a quick breakfast from our local bagel shop we packed the car and headed north, our eyes set on spending a few hours actively outside and/or by a beach. While we intended to visit Greenwich Point Park, we later learned that this is only for local residents are were turned away. We, however, did enjoy driving through the beautiful residential area near the shore. We instead settled on Cove Island Park in Stamford, which is a great park for bike riding, hiking, spending time at the beach, picnicking, and more.

After our visit to the park, we opted for some local ice cream and enjoyed a Blizzard by the local kosher-certified Dairy Queen in Stamford. (Kashrut: Vaad Hakashrus of Fairfield County) For those seeking lunch (or dinner) in Stamford, Six Thirteen is a popular option, a sit-down bistro serving huge burgers, steak, fish, sushi, cocktails, and more (Kashrut: OU + Vaad Hakashrus of Fairfield County), or Navaratna, a kosher vegetarian Indian cuisine restaurant located in downtown Stamford (Kashrut: Vaad Hakashrus of Fairfield County).

We left Stamford, heading east, and stopped in New Haven for dinner at the relatively new Fin & Scale. The restaurant opened in 2020 as a small but upscale sushi restaurant, offering delicious fresh fish, and drinks, amidst a beautifully designed space. This is a great date night spot in general, and also family-friendly so long as your kids like sushi. (Kashrut: Vaad Hakashrus of Fairfield County)

After leaving the restaurant we spent another hour on the road heading east towards our hotel in Mystic, CT.

We slept at one of the local Marriott hotels that’s 4 mins from the aquarium, where I used points for a free stay. Want to travel for free on points too? Check out our ”Favorite” 6 cards in the YeahThatsKosher credit card portal, all if which are great for earning free hotel stays and flights. The hotel included a free breakfast which often has fruit and kosher certified wrapped items.

DAY 2: We awoke early the next day to start our action-packed day exploring Mystic and the area. We started at the Mystic Aquarium, a fantastic facility great for both adults and kids. They open at 9am and can be fully explored within a few hours.

Just across from the aquarium is the Olde Mistick Village, a quaint shopping area with cute shops and places to grab a coffee. Since Mystic does not have any kosher restaurants, we used our time here to eat our packed lunches in the village before heading to Mystic town, less than 2 miles away. Down in Mystic proper, we spent some time at the Mystic Seaport Museum and then walked through town along the Mystic River. It’s a beautiful riverfront town with shops, a draw bridge, and beautiful riverfront vacation homes, inns, and rentals. I recommend parking in the Seaport Museum’s lot as it will save you time sitting in traffic further south and is at no extra cost.

While visitors to Mystic can easily spend another day here exploring at a more leisurely pace, we left Mystic around 4pm and visited the nearby Submarine Force Museum & the USS Nautilus submarine in Groton, where you can board and tour the partially submerged sub. This is a small museum and activity you can do in 30-60 mins depending on how quickly your group moves.

After the museum’s closure at 5pm we headed back west for dinner, stopping in New Haven again, this time at Ladle & Loaf, another relatively new kosher restaurant that opened in 2020. This restaurant serves a delicious mix of American and Middle Eastern dishes including burgers, shwarma, arayes, sabich, salads, and more. The food here offers great flavors for adults and kids alike.

Something we did not get a chance to participate in near Mystic was the TreeTrails ropes course and zip lining, which came highly recommended by locals for both their daytime and nighttime “Glow in the Park” activities (better for adults and older kids).

For those seeking to spend extra time in Southern Connecticut and potentially try more kosher options in the state, there are two more excellent restaurants to check out, one that opened in 2022 and one that’s been around since 1975.

Opened nearly 50 years ago in New Haven near Yale’s campus, Claire’s Corner Copia is a great brunch / lunch spot for dairy & vegan lovers alike. With its quirky menu and ample seating, this is a great spot to make for those passing through New Haven earlier in the day. (Kashrut: Vaad Hakashrus of Fairfield County)

As for the brand new kosher entry in CT, technically in Cos Cob, Greenwich & Delancey is the state’s newest kosher entry launched by the chef behind LOX in Manhattan, bringing a delicious take of old-school NY deli and Eastern European cuisines to this town near Westchester. (Kashrut: OU)