Mamaroneck is full of contradictions. Italian delis and pizza shops are just as plentiful as Asian fusion restaurants and whiskey bars. Boutiques attract customers who also shop at the town’s century-old toy store. And the stretch of shore along the Sound is home to private country clubs and public parks.
You’ll be tempted to have cake for breakfast at Maple & Rose (690 Mamaroneck Avenue; 914.222.4151). If you can resist the sticky buns and other assorted pastries on display, there’s plenty of lighter breakfast fare — avocado toast, breakfast panini, etc. — at this cozy all-day café.
Browse the mom-and-pop shops along Mamaroneck Avenue (everything from massive floral showrooms to tiny country stores), but make a point to stop in Miller’s (335 Mamaroneck Ave; 914.698.5070). In business for nearly 100 years, this iconic, family-run toy store stocks a wide range of summer-appropriate outdoor equipment and beach gear.
Pick up a picnic lunch. Order a classic Italian combo — thinly sliced imported meats, shredded iceberg, paper-thin rings of onion, and a splash of oil and vinegar, on a seeded hero — at Cosmo & Alex Pisano Bros. (252 Mamaroneck Ave; 914.381.4402). Then, pop next door to Boiano Bakery (258 Mamaroneck Ave; 914.698.2070) for a few of our favorite pignoli cookies. Or order a slab of ribs, some sides, house-made lemonade, and a tall stack of napkins to go from Smokehouse Tailgate Grill (320 Mamaroneck Ave; 914.341.1655).
Grab your vittles and make your way to Harbor Island Park at the base of Mamaroneck Avenue. The 44-acre waterfront park is home to a slew of perfect picnic spots, plus playgrounds, tennis courts, small gardens, and winding paths along the water’s edge. As the weather warms, visitors come here to get wet (you did remember to bring a swimsuit, right?) at a short swath of sandy beach and the kid-friendly sprinkler park.
Turn right as you exit the park, and it’s a 15-minute walk (or two-minute drive) to a cluster of niche shops along Boston Post Road. Stop by Katules (501 E Boston Post Rd; 914.341.1333) for tees, bags, and home goods printed with snarky sayings. Next door, Knit Shoppe’s (501 E Boston Post Rd; 914.630.7647) shelves are stacked high with a rainbow of high-quality yarns and knitting supplies. Then treat yourself to ganache-filled truffles and a wide selection of chocolate barks at nearby Chocolations (607 E Boston Post Rd; 914.777.3600).
Head back to Mamaroneck Avenue for pre-dinner drinks. Before the start of cocktail hour, stop into Siren (224 Mamaroneck Ave; 914.777.2122), for a selection of statement earrings, bold necklaces, and chunky cuffs.
Across the street Bar’Lees (157 Mamaroneck Ave; 914.630.7512) is one of Westchester’s hotspots for the bourbon boom. Sip a couple of the more than 100 whiskies behind the bar, or opt for one of the classic cocktails.
You can’t leave Mamaroneck without a trip to Walter’s (937 Palmer Ave; 914.500.5029). While lines stretch down the block at lunchtime, waits are much shorter now for the same split-and-griddled dogs slathered with mustard.