2 1/2-3 weeks North East - where to go?

Question

I have to be in Salem for a work thing in early November. I know it's not the ideal time to visit, but we'll have some time for a holiday. Thinking of flying UK --> Boston and then home from somewhere else. We'll have a 13 month old baby and no car (we can't drive).

Some ideas:

-Plane to Quebec – visit Montreal and Quebec (anywhere else possible with public transport?)

-Maine

-Vermont (I think we're limited to Burlington with public transport?)

-New York (we've been many times but would be returning – maybe visiting a few places nearby e.g. Sleepy Hollow.

-Travelling down to Washington and Virginia

We'd like to see nature, culture; I particularly like the more gothic/old worldliness aspect of the East Coast.

Any other tips?

Answer

Great trip window — early November gives you autumn color (in cooler pockets) and far fewer crowds than October. Since you’ll be flying into Boston, have a 13-month-old, and won’t be driving, I’ll focus on realistic, public-transport-friendly routes, baby-friendly travel tips, and a few itinerary ideas that match your “old-world / gothic” interest (Salem fits that bill nicely).

Quick reality check / transport summary

If you prefer comfort and fewer changes with a baby, trains and express intercity buses are your best friends in the Northeast. Long cross-country bus hops are cheaper but less comfortable; flights are fast if you want to jump between regions. There are direct intercity buses from Boston to Montreal/Quebec and to Burlington, VT, plus convenient coach links from Boston to many Maine towns (Portland and beyond).

Suggested trip shapes (2½–3 weeks, end somewhere else for departure)

Boston → Salem (work) → Coastal Maine loop → Montreal → Quebec City → fly home: Use Boston/South Station as your rail/bus hub. Concord Coach / other carriers link Boston to Portland and other Maine stops; from Portland you can catch buses north (or fly) to Montreal or take an overnight flight from Boston to Montreal/Quebec if preferred. This route mixes coastal New England, gothic seaside towns, and French-Canada culture.
Boston → Salem → Burlington (VT) → Montreal → Quebec City → NYC/DC (return south by Amtrak): Burlington is reachable by several intercity bus operators from Boston (Megabus/FlixBus/Greyhound); Burlington makes a nice quieter base for leaf watching and small-town New England charm. From Burlington you can head to Montreal by bus or train connections.
Boston → Salem → New York City → Hudson Valley / Sleepy Hollow → Washington, DC: If you’ve loved NYC before, use the city as a hub and take easy rail side trips (Metro-North to Sleepy Hollow and Amtrak down the Northeast Corridor to DC). This gives you gothic Hudson River towns, culture, and museums with minimal transfers.

How realistic is “plane to Quebec – visit Montreal and Quebec” without a car?

Very realistic: low-cost and scheduled long-distance buses run from Boston to Montreal (roughly 7–8 hours) and to Quebec City (often via Montreal / with transfers); or you can fly Boston–Montreal/Quebec for a quick connection if you prefer. Buses are generally the cheapest and fairly comfortable for overnight or daytime travel.

Maine (public transport friendly picks)

Portland — excellent food scene, walkable Old Port, easy bus from Boston (Concord Coach, Greyhound). Use it as a coastal base for day trips or a short overnight.
Ogunquit/Kennebunkport — more limited public transport, but reachable from Portland by local bus or arranged shuttle if you don’t want to change hotels a lot.

Vermont (what to expect without a car)

Burlington is the most reachable Vermont destination by bus from Boston (about ~4–4.5 hours on Megabus/Flixbus/Greyhound); from Burlington you can use local shuttles, taxis, or limited local buses to explore nearby scenic areas. Amtrak’s Vermonter serves parts of Vermont but does not (currently) go to Burlington proper — research combined bus+train to reach other towns.

New York / Hudson Valley / Sleepy Hollow

Boston → NYC by Amtrak (or budget flights) is straightforward and comfortable with a baby; NYC offers Metro-North trains north into the Hudson Valley and Sleepy Hollow (gothic, historic vibes) with minimal fuss.
If you enjoy “old-world” architecture and river-valley landscapes, base a few nights in Hudson or Beacon (train accessible from NYC) rather than a long drive.

Washington & Virginia by train

The Northeast Corridor (Amtrak) makes Boston→NYC→Philadelphia→Baltimore→Washington easy. From DC you can do day trips into historic Virginia (Alexandria is a short Metro ride; further afield requires either regional trains or a rented car/tour). With a small child, staying in walkable towns and using trains/subways is easiest.

Baby-friendly travel tips

Prioritize train travel for longer legs when possible — more space to move, easier bathroom access, and generally toddler-friendlier than buses.
Book seats/rooms with a little extra space (Amtrak business class or aisle seats on buses) and pick accommodations with a kitchenette so mealtimes are easier.
Pack a compact travel stroller and a baby carrier — both will be useful for cobbled towns and public transport.
Schedule travel days with plenty of buffer and avoid tight same-day multiple transfers; aim for one medium travel hop every 2–4 days.

Sample 18–21 day route (baby-friendly, public transport)

Days 1–3: Arrive Boston → short stay in Boston (acclimatize, pick up baby gear if needed), head to Salem for work commitment.
Days 4–7: Salem → Portland, ME (base), explore coast and food scene.
Days 8–11: Portland → Burlington (VT) or directly to Montreal by bus (choose one route to avoid backtracking).
Days 12–15: Montreal → Quebec City (or reverse) for French culture and architecture.
Days 16–18: Fly/Train back to Boston → NYC (or directly continue south by Amtrak) for last urban stretch; optional short Hudson Valley side trip (Sleepy Hollow, Beacon).
Final days: Travel down to Washington D.C. by Amtrak if you want the capital before flying home (or depart from NYC / Boston as suits your return flight).

Practical bookings & final tips

Buy long-distance bus tickets (FlixBus, Megabus, Concord Coach) in advance for savings and seat guarantees.
If you plan multiple Amtrak legs, compare rail passes vs. point-to-point — for the NEC (Boston↔NYC↔DC) point tickets are often simplest.
Weather in early November: chilly, variable, and earlier dusk — layers and waterproof outerwear recommended.
Since you like “gothic/old world” vibes: Salem (historic witch trial sites), Hudson Valley towns (old estates, river views, Sleepy Hollow), and Quebec City (walled old town) will likely be top match picks.

Bottom line

With no car and a baby, concentrate on a smaller number of hubs and use trains/buses between them: Boston → Salem → coastal Maine or Vermont/Burlington → Montreal/Quebec (if you want French-Canada) → finish in NYC or DC for easy international return. That gives a strong mix of nature, historic/gothic atmosphere, and culture without the stress of driving or too many complicated transfers.

2 1/2-3 weeks North East - where to go?

More Boston Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions