New Canaan
We like to kick start a fall day at Zumbach’s Gourmet Coffee (203-966-2704), which serves up a nice pumpkin-spice blend. Continue on to Waveny Park, where there are more than three miles of walking trails under a canopy of changing leaves. Also check out the Carriage Barn Arts Center; a show that opens September 18 features the work of 350 members of the New Canaan Society for the Arts (carriagebarn.org). Autumn is also a great time to visit the Philip Johnson Glass House (199 Elm St.) before it closes for the winter. The forty-seven-acre property takes on a whole new vibe at this time of year.
Darien
Start a lazy weekend with a satisfying brunch at Estia (1020 Post Rd.), where owner Colin Ambrose (who is from Darien) offers one of the most satisfying stacks of pancakes in town. Next, head to Pear Tree Point and pull up an Adirondack chair. In September, the Sound is still warm and very nice for a dip. The beach is generally pretty empty, too. If you think you need to cut the afternoon short to rush home and cook a meal, ease your mind. Simply stop off at Good Food, Good Things (865 Boston Post Rd.) and pick up the prepared beef bourguignon ($20 for two quarts) or chicken pot pie (priced at $24, it feeds four), both fine dishes for a fall evening.
Rowayton
Stop by Rowayton Market (157 Rowayton Ave.) for G.H. Macy & Co. teas provided by local chef Jamie Sydney, who has revived her husband’s family business—the brand was a popular import in the early twentieth century. After you’ve warmed up with a cup of George’s Afternoon Blend (a limited edition), walk around to Downunder Kayaking (203-642-3660), where you can rent a stand-up paddleboard for leaf peeping on Five Mile River. The location is open weekends, weather permitting, until Columbus Day. If you’d like to capture the colors of fall to enjoy all year round, sign up for a watercolor class at Rowayton Arts Center (145 Rowayton Ave.).
Farther Afield
Pumpkinseed Hill Farm (120 Beardsley Rd., Shelton) offers fifty varieties of pumpkins, gourds and squash in its market yard and pumpkin picking on twenty-five acres. Take a hayride and navigate the corn maze in a beautiful setting. Silverman’s Farm (451 Sport Hill Rd., Easton) has fifteen varieties of apples for picking, plus an animal farm with llamas, exotic birds and much more.
Rainy Days
Bring the kids to Chelsea Piers (1 Blachely Rd., Stamford). At the Jump Zone they can bounce out that extra energy on twenty-six interconnected trampolines. In Norwalk, Sono Field House (365 Dr. Martin Luther King Jr. Drive) has an indoor rock-climbing center for kids of all ages.