From Boston Logan International Airport, collect your rental car and drive north toward Derry—typically via I-93 North and NH-102, with your navigation app choosing the best route around traffic. Allow 1½–2½ hours door to door for baggage, the rental-car pickup, and the drive; leaving around midday should get you to Derry in the afternoon if your flight is on time. Expect possible tolls, and keep the rest of the day flexible in case of delays.
If you have daylight and energy, stretch your legs with a short walk at Alexander-Carr Park; November afternoons get dark early, so aim to arrive well before sunset and check local access conditions. Then head to downtown Derry to see the historic Derry Opera House from outside and stroll the compact town center. Performance access depends on the event schedule, so treat this as an exterior visit rather than counting on a show.
Settle in for dinner at Cask & Vine, a popular downtown spot; budget about $25–45 per person before drinks and tip, and consider calling ahead for a Friday-night table. It’s an easy end to an arrival day—no need to pack in more before heading to your friend’s place for the night.
Leave Derry around 7:00–7:30 a.m. to give yourself a cushion for Saturday traffic on I-93 South and garage entry; the drive can take 1¼–2 hours before parking. Park once in a central garage—check rates before you go, as a full day can cost $30–50 or more—then stroll through Boston Common for about 45 minutes. From there, walk north into Beacon Hill and give yourself an hour to explore its brick sidewalks and the Acorn Street area. It’s a residential neighborhood, so keep voices low and be considerate when taking photos.
Walk back toward Faneuil Hall Marketplace for a casual lunch and a browse. Allow about an hour; food usually runs $15–30 per person, depending on what you choose. The marketplace is generally open daily, but individual shops and food stalls keep their own hours, so check ahead if you have a particular stop in mind.
Continue on foot to the North End—roughly a 10–15-minute walk from the marketplace—and leave about 1½ hours to wander its Italian-American streets and stop at a bakery or café for a treat. Many North End spots get busy on Saturdays; a little patience is part of the experience. Afterward, walk back to the garage and allow 1¼–2 hours for the drive to Derry via I-93 North, plus extra time for evening traffic and the garage exit. Settle on a driver who’s rested for the return, or leave Boston earlier if you’d rather avoid a late drive.
After arriving in Salem, head first to the Salem Witch Museum downtown for a concise introduction to the 1692 trials. Check the museum’s current Sunday hours and whether admission is timed; book ahead if required, especially on a weekend. Allow about an hour, then walk to the Peabody Essex Museum. Two hours is a good visit without rushing; confirm Sunday opening hours and admission details before you go.
Walk to Ledger Restaurant, set inside the former Salem Savings Bank, for lunch. Budget around $25–45 per person before drinks and tip, and consider reserving a table. Its downtown location makes it an easy pause between the museum visits and the waterfront.
From Ledger, walk toward Derby Street for the House of the Seven Gables. Allow 1–1½ hours for the historic house and grounds, but check seasonal Sunday availability before building your plans around a tour. Finish at Derby Wharf: stroll toward the lighthouse for 30–45 minutes if the weather cooperates. Late November daylight is short, so aim to reach the wharf with time to spare; bring a warm, wind-resistant layer, as the waterfront can feel colder than downtown.
Leave Derry around 7:30–8:00 a.m. for Boston; allow 1½–2½ hours door to door, with traffic and parking the main variables. Park near the Museum of Fine Arts, Boston and keep luggage out of sight in the locked car; check Monday hours and admission details before you go. Spend about two hours choosing a few galleries rather than trying to cover the whole museum. Afterward, it’s a short walk to Christian Science Plaza for a look around the reflecting pool and architecture—allow roughly 30 minutes.
Walk from the plaza to Boston Public Library at Copley Square (about 10 minutes), and leave 45–60 minutes for the historic rooms and courtyard; visitor access can vary, so check Monday hours before setting out. Then return to the car, collect your luggage, and head to Logan International Airport. Aim to arrive by about 5:30 p.m. for your 8:40 p.m. flight to Chicago; allow extra time for Boston traffic and, if applicable, rental-car return, check-in, and security. Your flight time and any connection depend on your ticket.
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