Top Travel Days of 2023, Soaking Up the Sunshine and Skyline in Chicago

I spent my 50th birthday on Saturday biking with my extended family of ten on a guided day ride on the outskirts of Portland. Led by Norman Patry, owner of Summer Feet Cycling, we biked along the scenic shoreline of South Portland and Cape Elizabeth to five lighthouses. They included such picturesque gems as Bug Light, the smallest lighthouse in operation in America, and Portland Head Light, painted by the likes of Edward Hopper. Near Portland Head Light, we bought lobster rolls from a food truck and dined overlooking Portland Harbor. The lobster rolls were excellent, chockful of fresh meat, and you could order them Maine-style (with mayo), Connecticut-style (lightly buttered), spiced with curry (loved it) or wasabi. Washed down with locally made Eli’s Blueberry Soda and topped off with ginger molasses cookies from Standard Bakery in town, it was a perfect Portland meal. The ride ends at Kettle Cove, a small beach, just past Two Lights State Park. Summer Feet offers a slew of other bike trips in Maine including a self-guided 3-day ride near Kennebunkport that sounds enticing. But if you only have a limited amount of time in the state, this 5-hour ride gives you a good taste of Maine and comes highly recommended. 

The rugged and raw beauty of Maine has been a lure to many of America’s foremost landscape artists. Man versus the chaotic forces of nature, particularly fishermen struggling against powerful nor’easters, kept Winslow Homer busy on the boulder-strewn shores of Prouts Neck for more than two decades. Robert Henri, Edward Hopper, George Bellows, and Rockwell Kent all painted Monhegan Island’s 160-foot cliffs, meadows, and quaint fishing communities in their own distinctive styles like the bold black and white woodcuts by Kent. Monhegan is also a favorite subject of Jamie Wyeth, whose father Andrew Wyeth and grandfather N.C. Wyeth all summered on the Maine coast. Indeed, Andrew met his wife and her best friend Christina Olson in Maine. Olson is the woman lying down in the tall grass of Wyeth’s iconic painting, Christina’s World. 

The small strip of pavement forms a straight line into the horizon like an express route to freedom. Astride my bike, I zip over bridges and through tunnels, past large ponds, salt marshes and cranberry bogs, all while breathing in the sweet smell of spring wildflowers and the far more potent brine of the sea. The hum of traffic is gone, replaced by the call of the yellow warbler. The only obstacles before me are runners, clumsy rollerbladers, and other leisurely bikers. In the Cape Cod town of Orleans, I hop off my bike for a few minutes and take in that quintessential New England snapshot of fishing boats bobbing in the harbor. 

Cape Cod is so close to Boston that I often drive there on a day trip, which is exactly what we did yesterday to meet my cousin, Peter, and his family in town from Dallas. I took them on a ride we do each summer. We start on Main Street in Orleans in the lot next to Orleans Cycle and head out on the Cape Cod Rail Trail toward Eastham. Soon we pass the velvety marsh, where red-winged blackbirds sit atop the swaying cattails and cormorants dry their wings on floating docks. At Locust Road, we veer right off the CCRT and cross over Route 6 to reach the Cape Cod National Seashore Visitor Center. This is the start of a 2-mile bike trails that sweeps up and down through the forest and marsh, leaving you off at Coast Guard Beach, recently named one of the top 10 beaches in America. However, I think the beach up the road, Nauset Light, is even more scenic, backed by towering dunes. We lock up our bikes and walk down to the sweeping beach. Yesterday, there was at least 20 seals popping their heads out of the surf.