Amtrak Acela from Penn Station to Boston South Station takes approximately 3 hours 30 minutes; the Northeast Regional takes around 4 hours 15 minutes. The Acela is worth the premium for this journey length if availability allows. Book seats in advance, particularly for the return journey at the end of a long trip. South Station is in downtown Boston, a short walk or two subway stops from most central hotel areas.
Collect a rental car from Logan International Airport (10 minutes by water shuttle or 20 by Silver Line from South Station) for any onward travel to the South Shore, Newport or Cape Ann. In early November, weekend rental rates are lower than in summer and cars are readily available.
Four nights is enough for a proper Boston stay of two to three days followed by one or two nights in Newport, or alternatively a slower Boston itinerary without the road component.
Boston
Boston is a walking city in a way that few American cities are: the historic core is compact, the Freedom Trail is a red line on the pavement, and most of the main sites are within a mile or two of each other. On post-marathon legs, this means the city is genuinely manageable at slow pace without requiring a car or constant taxi trips.
The Freedom Trail is a 2.5-mile self-guided walking route marked by a red line through the pavement or a line of red bricks, connecting sixteen historic sites from Boston Common to the Bunker Hill Monument in Charlestown. Completing all sixteen sites in one day is ambitious on fresh legs; doing the central section from the Common to Faneuil Hall and the Old North Church, skipping the Charlestown section, takes about two to three hours and covers the most significant points. The trail is flat for most of its length, with one steep section up Copp's Hill in the North End.
The Boston Marathon finish line is on Boylston Street between Dartmouth and Exeter Streets, marked by a set of blue and yellow painted stripes across the road and a banner position that is reinstated each April. In November the finish line itself is painted on, permanent on the road surface; the surrounding block has the Boylston Street stores and the John Hancock Tower above it. For anyone who has run New York for the first time and is already thinking about Boston, standing at the finish line in November is a useful reference point.
Boylston Street and Back Bay
The Back Bay neighbourhood, running westward from the Public Garden along Boylston and Newbury Streets, contains the largest concentration of independent shops, restaurants and cafés in central Boston. Newbury Street is eight blocks long and fully walkable; the street descends gradually from the Massachusetts Avenue end toward the Public Garden. The Trident Booksellers and Café at 338 Newbury Street is a secondhand and new bookshop with a café and is the correct choice for a slow post-race afternoon.
Brasserie Jo (120 Huntington Avenue, in the Colonnade Hotel) is a French brasserie within walking distance of the marathon finish line and one of the more reliable options for a sit-down recovery dinner.
Harvard and Cambridge
Cambridge is accessible from central Boston by Red Line subway (approximately 20 minutes from Downtown Crossing to Harvard Square). Harvard Square itself is the standard destination: independent bookshops, cafés along Massachusetts Avenue, and the university campus directly adjacent. The Harvard Art Museums (32 Quincy Street, entry approximately $20) occupy a Renzo Piano building opened in 2014 and contain the university's combined art collections including the Fogg, Busch-Reisinger and Arthur M. Sackler museums. It is a flat building with seating and a café; a 90-minute visit at recovery pace is comfortable.
Newport, Rhode Island
Newport is 70 miles south of Boston by Interstate 93 and Route 24, approximately 90 minutes by car. The Cliff Walk is a 3.5-mile public footpath along the coast between the beach at Easton's Beach and Bailey's Beach, running past the back terraces and lawn edges of the Gilded Age mansions. The path varies between smooth tarmac and rough coastal rock; the rocky section in the middle and south should be avoided on tired legs immediately after a marathon. The smooth northern section from Easton's Beach to the Vanderbilt estate at Rough Point takes about 45 minutes each way and gives the best views of the Atlantic with the least technical walking.
The Breakers (44 Ochre Point Avenue, entry approximately $36), the Vanderbilt family's 70-room summer cottage built in 1895, is the most visited of the Newport mansions. It is open year-round and significantly less crowded in early November than in summer. The interior contains the kind of excess that requires a guided audio tour to fully parse: three-storey great hall, 20-foot ceilings in the dining room, bathrooms with both fresh and salt water taps.
Newport's waterfront (Thames Street and America's Cup Avenue) has a working harbour with restaurants and independent bars. Fall closing times are earlier than summer; check ahead for specific restaurants on a weekday.
Getting Back to New York
Amtrak from Boston South Station to Penn Station. Return the rental car to Logan Airport and take the Silver Line or water ferry back to South Station with sufficient time before departure. Alternatively, Amtrak also runs from Providence, Rhode Island (40 minutes south of Boston by commuter rail), which allows a different routing if the Newport leg ends there. Book the return journey before leaving New York.