Trips & Special Activities

Sheffield Island Day Trip: Thursday, June 30


Spend the day on Sheffield Island! The island offers abundant summer fun for guests who visit the 150 year old lighthouse, beaches, and the wildlife refuge. This trip’s experience is one of the most exciting tours that the Norwalk Harbor Islands area has to offer. You’ll step directly from the boat and into the past. Sheffield Island is located in the outer reaches of Norwalk Harbor and provides unique views of New York City and the surrounding waterways.

Every summer, the Norwalk Seaport Ferry carries hundreds of passengers to the historic 1868 Sheffield Island Lighthouse for their famous Clambakes! This Clambake will prove to be a true New England dining experience. This trip’s menu will include a choice of: Rosemary Marinated Chicken Breast (with Summer Tomato Bruschetta), Marinated Rib Eye Steak, Teriyaki Marinated Atlantic Salmon, vegetarian Burger, or Vegetarian “Chicken” Breast (pick one at check-out). All main course items come with: Mixed Field Green Salad, Steamed Clams, Mussels, Corn on the Cob (with Lemons and Drawn Butter), Roasted Red Potatoes, Cole Slaw, Grilled Summer Squash with Fresh Thyme, Dessert, Lemonade, and Iced Tea.

In addition to dinner on the island, this outing experience includes a roundtrip ferry ride, a tour of the Sheffield Island Lighthouse, and panoramic views of Long Island Sound. The island also has walking trails for those who wish to explore.
Sheffield Island is a rocky outcrop with rolling terrain. Please wear comfortable, closed-toe shoes with a closed heal or back strap to keep the shoes on the feet. Due to safety concerns, flip-flops are not allowed.

Gloucester Lobster Cruise: Wednesday, August 3


Step aboard the elegant Beauport Princess and settle back in luxury for a cruise from one of New England’s most photogenic harbors, Gloucester, MA. Cruise historic Gloucester Harbor which is the oldest fishing community in the
United States.

Enjoy your lobster buffet lunch while cruising past downtown Gloucester with its historic homes, churches, and city hall. The scenery is best seen from vantage viewpoints on the ship’s deck. Among the sights are Ten Pound Island Lighthouse,
Blynman Bridge, Gloucester Fisherman’s Statue, Hammond Castle and Norman’s Woe, a rock reef immortalized in the “Wreck of the Hesperus” poem. Your Traditional New England Lobster Bake Menu includes: Freshly Baked Rolls; New
England Clam Chowder; Steamed 1 ¼ Pound Lobster, Barbeque Chicken, Corn on the Cob, Red Bliss Potatoes, Cole Slaw, Dessert.

Once back on land, you will head off to Rockport, MA, one the country’s oldest artisan colonies. Have some time to walk around and enjoy the shops and the art museums. If you just want to sit and enjoy looking out over the harbor, you can do that too.

Providence, RI: Italian Style: Tuesday, September 13


Head to Providence’s Little Italy, where the day’s activities will certainly make you feel as though the bus flew you across the ocean!

Join your tour guide for a behind-the-scenes tour of Providence’s Historic Federal Hill. Your senses will be intoxicated with the flavors, smells, sounds, and sights of Italy. You will see why Federal Hill is described as “One of the top ten Little Italy’s in America.” After, enjoy a three-course lunch at Cassarino’s Restaurant. Lunch begins with Bruschetta and you have the choice of: Pollo Parmigiana, Penne Primavera, or Baked Fish, followed by Coffee and Dessert. (please advise meal selection at time of booking)

The Italian experience continues onboard an original Venetian Gondola, where you can view the historical sights of the Renaissance City from a truly unique vantage point. Glide under the magnificent Italian-influenced bridges while observing the illustrious beauty surrounding the Riverwalk. A little singing by the gondolier will complete the experience.

Sit along the Riverwalk listening to live music with an Italian flair. The music, covered bridges, magnificent architecture, the food, and gondolas will certainly transport you to Italy. In sitting along the Riverwalk, some benches are provided. If you would like to bring a chair to sit in while listening to music, you are more than
welcome to do so.

Autumn Railway Experience in the Berkshires: Tuesday, October 11


First stop, we will be taking a scenic narrated train ride through the Berkshires with the Berkshire Scenic Railway. Enjoy the sights on this 10 mile round trip ride. This train ride is a living history exhibit that explores the rich railroad history of the region and complements the already popular cultural attractions located in the Northern Berkshire area.

Enjoy lunch at Michael’s Restaurant. For your entrée, please select one of the following: Turkey and Cheese Wrap, Tuna and Tomato Wrap, Ham and Cheese Wrap, Grilled Chicken Wrap, or a Veggie Wrap. All meals include Chips, a Pickle, Soda or Iced Tea.

After lunch, we will head over to Balderdash Cellars. Founded in 2011, Balderdash Cellars is a boutique winery located in the beautiful Berkshires of Western Massachusetts. They focus on producing ultra-premium wines from grapes grown by world-class California vineyards. Here will we will have a tour and tasting!


Daytime Mall & Shopping Trips- In an effort to meet your needs, the monthly “Daytime Mall Trips” include drop-offs and pick-ups at nearby stores. (see Windsor Seniors’ Newsletter for current dates/times/destinations of trips) Please call 860-285-1846 by noon at least 2 days in advance to sign up for the mall trips.

Evening & Weekend Trips-  The Windsor Senior Center has a variety of evening and weekend trips for your pleasure.  Please call 860-285-1992 to sign up. Transportation available from your home; cost of meals and/or fees are your responsibility.

Casino Trips- (RETURNING SOON) Every third Friday of each month, the Windsor Senior Center has a motorcoach bus trip to either Foxwoods Casino or Mohegan Sun (destination and times alternate each month, please call Senior Center for details).  Cost is $25.00, which includes coach bus transportation, gratuities, $15 meal coupon, $15 slot play.  Sign up in the office, online, or call 860-285-1992, at least 10 days in advance of scheduled trip.

Early Bird Suppers- Our popular Early Bird Suppers take place on the last Tuesday of each month (unless otherwise specified), from 5:00 PM to 6:30 PM.  Sponsored by various supporters from the community, please sign up in the Windsor Senior Center office, online, or call 860-285-1992.  Reservations required.  Menu varies.  (see Windsor Seniors’ Newsletter for menu)

Rise ‘n Shine Breakfasts- A delicious breakfast is held at the Windsor Senior Center every other month. Reservations required.  Limited to 50 people.  Free!

Birthday Lunch Celebration- Come celebrate your birthday at the Windsor Senior Center on the last Wednesday of each month from 11:45 AM to 12:30 PM. Free cake, donated by Geissler’s for everyone.  Birthday gifts to Senior Center members also provided. You must register if it is your birthday to receive a gift. Please call 860-285-1992 to register.

*Returning in May 2022* AARP Driver Safety Classes- The Windsor Senior Center holds the Driver Safety Program, hosted by AARP, on the first Monday of every other month, 9:00 AM to 1:00 PM.  Anyone age 50 or older may take the class.  This course qualifies you for lower insurance rates in CT. $20.00 AARP members / $25.00 non-members.  You must register, as class size is limited to 20 students. Please call 860-285-1992 to register.