Located only an hour and a half from New York City, Old Saybrook, Connecticut is one of the New England state's oldest towns. It also happens to be the only town in Connecticut with a downtown along a waterfront. Being one of those New Yorkers with no car, my weekend trip started with renting a luxury Audi A4 from the Silvercar rental app. I picked up my silver sedan from the lot in Columbus Circle and jetted on my way on the Westside Highway. Upon my arrival at Old Saybrook an hour and a half later, I saw that the destination is a classic old town with old town charm. Unlike many old towns that are run down, almost abandoned, or dilapidated, Old Saybrook is a luxury small town shopping and wellness experience against a backdrop of pretty fields and manicured landscaping.
At the Saybrook Point Inn & Spa, it was a treat to reside along Connecticut’s waterfront and wake up to peaceful marina views with small boats swaying in the gentle breeze. The 82 spacious guest rooms range from standard rooms to luxury suites, with access to the substantial-sized pool; fitness center; Fresh Salt restaurant; and on-site spa. I also woke up to take early 8am yoga in the designated yoga studio. The icing on the cake was ordering charcuterie while having wine on my room’s outdoor balcony from one of the hotel’s cottages.
As I drove down the main shopping strip along Main Street, there were picturesque, old vintage signs that are intermittent like Saybrook Hardware Co., Old Colony Package Store, and Pittsburgh Paint. Stop in boutique shops and purchase candles and nick knacks at the Little Gift Shoppe or handcrafted Georgian mirrors and vintage Navajo paintings at Maximus Antiques Home Décor. At Esty's, vintage lampshades dominate the store run by second generation, Susan Esty, who has been refurbishing old lighting for 48 years. If you're wondering what kind of footwear is suitable for trekking the New England fall weather? I wore my leather Mohinders, which kept my feet both cushioned and stylish while walking around the several blocks of Main Street.
For those looking to get active or just happen to be training for a 10k or half marathon (like I was), from the Saybrook Inn, you can turn right from the hotel and run down the causeway where white, painted “Fishing” signs are demarcated in white letters on the concrete. Fishermen are out early with seagulls swooping overhead with morning catches in their talons. Run past “Important Ecological Area” signs protecting tall ferns and flowering plants over marshland. Run more miles past exclusive, quiet communities with private beaches like Fenwich and then through the neighborhoods of Old Saybrook where dog walkers and retirees get their steps in.
You can also learn to kayak or standup paddle board with Black Hall Outfitters. Along the Connecticut River, there is one of the most undeveloped inlets as far as industrialization on a major river. The waterway was beautifully preserved as a wildlife refuge because it is so shallow. When you are kayaking or standup paddle boarding, take in birds like osprey, falcon, sharp shinned hawks, as well as people fishing and crabbing on small boats.
Caffe Marche is one of the premier new, dining establishments in Old Saybrook. The décor features exposed brick ceilings in an original 1740 building that started as a tavern and became a pharmacy thereafter. The most famous owner was Anna James, whose father escaped slavery at 16. She went on to become the first African American female pharmacist in Connecticut, while her niece Anne Petry was the first African American woman to sell more than a million copies of a book. As you take in the history, sample the Marchigiani cuisine from the owner Paul's hometown, Marche, Italy like burrata and gnoccci using local ingredients from Connecticut.