Weekend beach getaways are a staple of summer travel, but Madison, Connecticut offers so many things to do, you will want to return year round.
I spent a rainy weekend in seaside Connecticut, a ‘one tank trip’ from New York City, Boston, and much of the Northeast. And though rainy weather thwarted some of our plans, we were able to fill our time with museums in nearby New Haven, boutique shopping in the small towns along the shore, and eating well. What more could you want? (Um, sun?)
Writer was hosted by the hotel.
Hit the Beach

In the small window of dry weather we hopped on the bicycles provided by The Homestead, the charming B & B in Madison where we spent two nights. East Wharf Beach, just a mile from The Homestead. In season, the B & B has parking passes for Hammonasset Beach State Park. The state park is about 3 miles away, and has extensive walking and biking trails as well. I had planned to run there but the weather deterred me. So I will have to return!
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Day at the Orchard

Bishop Orchards has seasonal pick your own fruit, a cider mill, winery, farm market and bakery. Best of all is the creamery, where all the soft serve is vegan, made with oat milk. The produce sold here is either grown on site or from local farms, and the pick your own ramps up in June with strawberries.
I could not resist the I 95 Traffic Jam, with peaches, strawberries, cherries and raspberries cranberries. There was also Frog Jam: figs, raspberries, orange and ginger.
Culture Time

New Haven has a bunch of museums, and the ones operated by Yale University are free.
The Yale Peabody Museum recently reopened after an extensive renovation. The building is now much more accessible and energy efficient. This natural history museum has dinosaurs, rocks and minerals, fossils and artifacts from ancient cultures.
We visited the Yale Center for British Art, which has the largest collection of British art outside the UK to see the Turner exhibit. This museum also just reopened after a two year renovation.

We spent much of the afternoon at The Yale University Art Gallery, the oldest university art museum in the US. The museum has a rooftop terrace and a sculpture garden (alas, closed because of the rain). But we saw a couple of photography exhibits and explored the historic architecture throughout.
You can literally spend the entire day walking from museum to museum. There is also the New Haven Museum, but it is closed on Sundays (and it charges $4 admission). I was intrigued by the exhibit, ‘From Clocks to Lollipops: Made in New Haven,’ so – next time!
The diverse student and faculty population in New Haven may be why the city has so many different cuisines. We had lunch at Hanvely, a cafe and non-profit that trains immigrant women for the workforce. The Middle Eastern food was delicious and we liked supporting the cause.
Time for Fun

Thimble Island Brewing Company, in Branford, has weekly trivia, live music, a dog friendly outdoor patio, and a wide selection of beers on tap. It also has burgers, pizza, wings, and soft pretzels. Chamard Vineyards, a winery in Clinton, has a bistro, a tasting room and beautiful vineyards you can tour (but not appealing in the, you guessed it, rain). Chamard and Bishop Winery are part of the CT Wine Trail.

But we were happy to wander from shop to shop in Madison, with a large, independent bookstore, RJ Julia Booksellers, that also has a cafe. And we checked out local antique stores and the charming gift shop Junk-2-Junque. And the historic buildings are also quite beautiful.
From Southern CT to Southern Indian

Sheerkan Indian Street Food specializes in food from Southern and Central India. There is a broad range of vegetarian food, and meat if you are so inclined. And the cocktails are first rate. The restaurant is practically on the Yale campus, so the crowd skews young.

You could lose yourself for days at Page Hardware, in nearby Guilford, where this family owned institution has everything a DIY-er could need, plus high end appliances for the most discerning home cooks. More like a general store, Page has everything from cleaning products to knife sharpening, heirloom seeds to high-end induction cooktops.
My husband gets hives when we go to The Home Depot, but he enjoyed the low-key vibe here.
It would be very easy to bike to other towns, and even to New Haven; the back roads have wide shoulders and the few drivers who passed us were very considerate.
Thoughtful Touches at The Homestead

The Homestead also has two free electric vehicle chargers, so your one tank trip will cost you nothing if you drive an EV. There are also umbrellas you can borrow, (sadly, we needed them) beach towels and blankets, and games you can play in the welcoming living room.
Why You Should Stay at The Homestead

- Large comfortable king-sized bed, with an electric fireplace.
- Vitamin C & E infused water in the shower
- Healthy and filling breakfast
- All day snacks, including an espresso machine, cookies, fruit, nuts and make your own popcorn
- Afternoon/nightly port
- Great selection of albums you can play on the record player in your room
- Dog friendly rooms
- People friendly owners/caretakers. You really feel valued as a guest
- Free bicycles
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