With beaches, that famous fall foliage, and an array of stylish new cafes and cultural attractions, Connecticut’s southern shore is ripe for exploration. And a train excursion down makes for an easy car-free escape from New York or Boston.

Credit: Shore Line East / Connecticut Department of Transportation

This year, the Shoreline East, Connecticut’s under-the-radar local railway whose cheery conductors know regulars by name, celebrates 25 years chugging along the 45 miles between New Haven and New London. Though designed for commuters, the train passes through picturesque marshlands, dense forests, and historic waterfront villages combining New England charm, old world flavors, and stylish new attractions—perfect for a fall weekend getaway. Intrigued? Read on for the ideal itinerary:

Day 1 (Afternoon): New Haven to Guilford

Insiders know that the Elm City, which saw a wave of Italian immigration in the early 20th century, has the best pizza on the East Coast. For a pre-train pick-me-up, choose one of two local favorites: Frank Pepe Pizzeria Napoletana or Sally’s Apizza, both serving slightly crisp, coal-oven-baked, traditional “ah-beetz” (“pizza,” in Neopolitan), and both walking distance from State Street Station. A 20-minute jaunt on the Shoreline East brings you to Guilford, an historic New England village overlooking the Long Island Sound. Explore the charming downtown and town green before dinner at The Place, a classic seafood shack where patrons bring their own beer or wine and nosh on lobstah rolls al fresco around a big fire. There are two simple but well-run Bed & Breakfasts in Guilford: the rural B&B at Bartlett Farm (from $145/night) and the hilltop Sound Reach Bed & Breakfast (from $125/night).

Day 2: Guilford to Madison

The airy butter croissants at Guilford’s two-year-old Hen and Heifer sell out within an hour of opening at 8 a.m.; late risers should find that locally sourced coffee, homemade granola, and crumbly coffee cake will do the trick. Twenty minutes away (divided between the train to Clinton station and then a taxi ride) is Hammonasset State Park. With its long stretch of yellow sand punctuated by rocky outcroppings, natural dunes, and temperate water, it’s hard to believe you’re still in Connecticut. For an authentic dejeuner, head to nearby Madison for Bar Bouchee, owned by the French proprietors of New Haven’s lauded Union League Café. Also in Madison Center you’ll also find RJ Julia Booksellers, that rare thing—a thriving independent bookstore—with readings and children’s literary events, and the restored 1912 Madison Art Cinemas. Field House Farm, a family-run farm just outside Madison, hosts literal field-to-table dinners at its 1720-era farm house, where you’ll find chickens, heritage turkeys, Shetland and Hampshire sheep, goats, pigs, a llama, and a donkey. As for where to stay, Hilton’s new waterfront Madison Beach Hotel is short on charm but long on beachy views, spa treatments, and crisp, clean guestrooms.

Day 3: Old Saybrook to Branford to New Haven

Scenic Old Saybrooke, 30 minutes from Madison on the Shoreline East, is one of the oldest towns in Connecticut, found in 1635. In addition to its iconic white lighthouse, it’s also the hometown of renowned actress Katharine Hepburn; her legacy was honored in 2009 with The Kate, a live theater and cultural center housed in the reconditioned turn-of-the-century town hall. Nearby, don’t miss the outstanding cheese shop, Fromage Fine Foods, with more than 100 cow-, goat-, and sheep-milk varieties, plus coffee and olive oils. Further down Boston Post Road is Atlantic Seafood, a first-rate fish market whose friendly owners also prepare housemade seafood soups and stews. If you have an extra day, head onward to the end of the Shoreline East to pretty, littoral New London. Otherwise, start doubling back westward toward New Haven, leaving several hours for one last stop in sleepy Branford (30 minutes from Old Saybrook on the Shoreline East). From there you can explore the aptly-named Thimble Islands, a collection of several dozen tiny, rocky isles ranging from just-large-enough-for-a-mansion to the 19-acre Horse Island, where Yale runs an ecology lab that’s open to the public. Stony Creek Kayak offers guided kayak tours of the archipelago. Back in Branford Center, the green-painted, Lyon-inspired Le Petit Café has been winning over diners and food critics for almost two decades; its four-course $55 dinner is still a fantastic value. For simpler fare, the Lobster Shack on Branford River offers grilled clams, lobster rolls, and seafood chowder. Walking distance from the Branford train station, a meal there is an ideal way to end your tour of coastal Connecticut.

Getting There

The Shoreline East runs from New Haven to New London, both of which can be reached via Amtrak; New Haven Union Station is also served by the MetroNorth commuter railway.