Old Cutler Trail in South Miami is both a botanical and architectural experience, with lush vegetation and spectacular residences in an upscale district. Its 11-mile (18-kilometer) length includes a variety of attractions including parks, preserves, a garden and numerous estates. Stop at many of these to sample what the prime real estate Miami neighborhoods of Cutler Bay, Palmetto Bay and Pinecrest have to offer.
Whether you start the trail at the north end in Miami or the southern tip in Cutler Bay, you’ll immediately notice the trees that separate the trail from Old Cutler Road, which provide welcome shade. The varieties are mostly big-rooted banyan and ficus, with an array of colorful flowers growing under the canopy.
Closer to the northern end, Matheson Hammock Park is popular for its beach on a lovely ocean lagoon. Plan to stop at Fairchild Tropical Botanic Garden, a horticulturalist’s dream for tropical plants. Families will find lots to do in this lush setting.
Pinecrest Gardens makes an interesting stop, where art and nature blend together and music and dance activities often occur. On any Sunday, shop at the market for delicious food items and plants.
Continue along the trail past other parks, estates and schools to arrive at the Deering Estate. Its founder, Charles Deering, was involved with manufacturing agricultural equipment. The estate is now a historic site offering land and water tours, as well as other family-oriented activities.
The trail connects to many others, such as the northern end’s Commodore Trail, Red Road Trail and Biscayne Trail at the opposite end. Restrooms are provided along the trail. Take water, sunscreen and food, as the area is primarily residential. Find Old Cutler Trail’s northern end where Old Cutler Road, Cocoplum Road and SW 42nd Avenue meet in Coral Gables, or the southern trailhead where Old Cutler Road and SW 87th Avenue converge in Cutler Bay. Park near the northern trailhead at Cocoplum Circle or a little farther south at Matheson Hammock Park. The trail is accessible and free.
