As you’re leaving Rochester (nicknamed “The Flour City” as it was once one of the largest producers of flour in the world), follow New York State Route 31 into the village of Pittsford to pay homage to one of America’s first great transportation routes: the Erie Canal. When it opened in 1825, the canal connected goods and commerce from the Hudson River in Albany to Lake Erie in Buffalo – and led to the growth of a host of communities like Pittsford along the way. Pittsford features a quaint business district filled with shops and restaurants centered around the canal. Grab a cone from Pittsford Farms Dairy, which has been owned by the same family since the 1940s and bottles its own milk used for its scratch-made ice cream, then walk along the cross-state Erie Canal Trailway.
From Pittsford, continue following State Route 31 into the countryside, where it winds its way near and along the canal to Palmyra – the birthplace of the Church of Jesus Christ of Latter Day Saints. Much of Palmyra’s religious history remains remarkably intact nearly 200 years later for visitors to explore, from the homestead of church founder Joseph Smith to Hill Cumorah, where Smith encountered religious visions, and the Grandin Building print shop in the village that first published the “Book of Mormon.”
At Palmyra, turn onto State Route 21 South and drive into the city of Canandaigua at the western end of New York’s Finger Lakes, one of America’s most renowned wine and grape growing regions. A great introduction to the bounty of the Finger Lakes can be found at Canandaigua’s New York Kitchen, a not-for-profit offering cooking classes, a restaurant filled with farm-to-table menu options and a tasting room featuring more than 60 wines from across the state. Enjoy a glass of wine, then take a walk along Canandaigua Lake found right outside.
An off-trail detour worth the trip can be found 20 miles south of Canandaigua on State Route 21 in the village of Naples, which features two bakeries – Cindy’s Pies and Monica’s Pies – renowned for their grape pies sourced from surrounding vineyards. Otherwise, pick up U.S. 20 East and stay on it through the heart of the Finger Lakes region.
As U.S. 20 leaves Canandaigua, it narrows into two lanes and becomes one of New York’s great open roads, passing by vintage diners, ice cream stands, farm shops and quaint lakeside towns along the way. While the drive to Syracuse takes less than two hours, the Finger Lakes region alone is worth exploring for at least a couple of days.
Take a scenic detour off of Route 20 on N.Y. 14 South, which connects the city of Geneva and village of Watkins Glen alongside sweeping vistas of Seneca Lake. Or proceed down N.Y. 89 South for a similarly stunning drive alongside Cayuga Lake to Ithaca, a bustling college town filled with cultural amenities and surrounded by waterfalls, gorges and hiking trails at Robert H. Treman and Taughannock Falls State Parks that resemble scenes straight out of Middle Earth. Sip your way down each lake with tastings at dozens of wineries on the way; the combination of Rieslings, Chardonnays and incredible views is a bucket list, not-to-be-missed New York experience.
Return back the way you came and proceed on U.S. 20 East to continue on the trail. Just before hitting the village of Waterloo, stop at Mac’s Drive In (open April-September), which has sold Rochester’s own smooth, sweet Richardson Root Beer that’s produced in small batches since the stand opened in 1961. The root beer float – served in a chilled mug and topped with soft serve – might just be one of the best anywhere. In Waterloo, grab a bite to eat at Connie’s Diner, which dates back to 1963, has been under the same ownership for more than 30 years and serves breakfast all day.
Heading east, you’ll enter the village of Seneca Falls, where suffragists Elizabeth Cady Stanton and Lucretia Mott changed the course of American history in 1848 by organizing the Seneca Falls Convention. The pivotal gathering produced the Declaration of Sentiments that advocated for gender equality and paved the way for women to gain the right to vote decades later. Retrace the steps of the suffragists who gathered in Seneca Falls at the Women’s Rights National Historic Park, which features a museum and the Wesleyan Chapel that hosted the 1848 convention; the Elizabeth Cady Stanton House near the eastern end of the village is also open for tours.
There’s a reason why driving into Seneca Falls might feel instantly familiar. Filmmaker Frank Capra based the setting for his 1946 classic “It’s a Wonderful Life,” the idyllic community of Bedford Falls, off of this village—right down to the steel truss bridge spanning Seneca Creek. Learn about the ties between the village and the movie at the It’s a Wonderful Life Museum.
If all that history and sightseeing worked up an appetite, stop by Reese’s Dairy Bar in between Seneca Falls and Auburn. This family-owned roadside stand has been making its own ice cream – from peanut butter mud pie and caramel apple to pumpkin and cotton candy – since 1973, as well as a variety of grilled favorites like Central New York’s own Hoffman Hot Dogs.
Once arriving in the city of Auburn, take a quick detour off of U.S. 20 and proceed down South Street, which features the homes of two of the most influential Americans of the 19th century. Harriet Tubman spent the last decades of her life in a house on the outskirts of Auburn following her years of helping escaped slaves along the Underground Railroad. Tubman bought the land to build her home from abolitionist William Seward, who became Secretary of State for Presidents Abraham Lincoln and Andrew Johnson and negotiated the purchase of Alaska. The Harriet Tubman House and Seward House Museum bring the stories of these towering American figures to life.
Following Auburn, slow down and enjoy the view in the village of Skaneateles. This popular Finger Lakes getaway on Skaneateles Lake has a walkable business district centered along U.S. 20 filled with shops and restaurants. Walk through the village’s Clift Park and onto its pier for a panoramic view of the lake. Then save room for dinner at the iconic Doug’s Fish Fry (See Syracuse section.) Skaneateles is the kind of place worth stopping and staying awhile; the 1807 Sherwood Inn is the perfect spot for an overnight.
After U.S. 20 leaves Skaneateles, it winds its way through a series of rolling hills – Central New York’s apple country. A series of orchards and farm stands line this section of the trail like Beak and Skiff Apple Orchards. Beak and Skiff has grown since its founding more than a century ago to include 300,000 apple trees, a bakery, distillery, general store and hard cider tasting room. Make sure to try a homemade apple fritter at the bakery when they are in season.
Continue on U.S. 20 for seven more miles until reaching Interstate 81, then follow the highway north for the final 10 miles into Syracuse.