New England in late September is a tapestry of crimson maples, gold birch, and slate-blue Atlantic. This road trip traces the historic coast from Boston to Cape Cod and Nantucket, then north through Maine’s lighthouses and fishing harbors to Acadia National Park—balancing scenic drives with memorable meals and unhurried, two-night stays.

Boston’s Revolutionary War landmarks and world-class museums set the stage before you sweep down to dune-backed beaches and saltbox villages on Cape Cod. A ferry hop delivers cobblestoned Nantucket. From there, Maine’s food scene takes a star turn: oysters and brown-butter lobster rolls in Portland, gallery-rich Camden, and granite peaks meeting surf in Acadia.

Practical notes: Expect crisp mornings (50s°F) and mild afternoons (60s–70s°F). Book ferries, dinner reservations, and national park times (Cadillac Mountain) in advance. Coastal foliage typically begins in late September, with color arriving earlier the farther north you go—perfect for this northbound arc.

Boston

Days 1–2: Arrive and explore Revolutionary Boston, seafood classics, and harbor views

Founded in 1630, Boston is a compact city best explored on foot. Follow the brick-paved Freedom Trail, browse the Back Bay brownstones, and end your day with a harbor sunset and a buttered lobster roll—a delicious prologue to your coastal drive.

• Getting in (Seattle to Boston): Nonstop and 1-stop flights run 5.5–7.5 hours. Typical late-September fares run ~$300–$650 roundtrip. Compare options on Trip.com and Kiwi.com. Pick up your rental car on Day 3 to avoid city parking fees.
• Top highlights: Stroll the Freedom Trail, Beacon Hill’s gaslit alleys, Boston Public Garden swan boats (seasonal), and the MFA or Isabella Stewart Gardner Museum. For sports fans, a guided tour of Fenway Park adds a dose of Americana.
• Coffee & breakfast: Tatte Bakery & Café (almond croissants, shakshuka); Flour Bakery (sticky buns and breakfast sandwiches).
• Lunch (lobster roll radar): James Hook & Co. (classic hot-buttered or cold-with-mayo), Neptune Oyster (also famed for oysters), or Row 34 (buttery split-top roll, craft beer).
• Dinner: Select from Uni (creative sashimi and jaw-dropping maki), Mamma Maria in the North End (quiet, white-tablecloth Italian in a cobblestone square), or Grill 23 (Boston’s grand steakhouse with an excellent raw bar).

Curated activities in Boston (choose 2–3):

• Boston Hop-On Hop-Off Trolley Tour with 13 Stops

  

  Effortless way to cover key neighborhoods with narration; hop off for the North End, Beacon Hill, and the Seaport.

• Boston: Freedom Trail History Small Group Walking Tour

  

  Expert-led deep dive into Revolutionary sites—perfect context before you venture up New England’s storied coast.

• Boston Harbor Sunset Cruise

  

  Golden-hour harbor views past Fort Independence and the city skyline—bring a light jacket.

• Boston North End Food Tour of 6+ Tastings, Cannoli, Lobster Roll

  

  Sample the best of “Little Italy” with stories, cannoli, and—yes—lobster roll tastings.

Where to stay (4–5 stars): Consider The Newbury Boston (classic, overlooking the Public Garden), Four Seasons Hotel One Dalton Street (sleek, Back Bay), XV Beacon (boutique, Beacon Hill), or Fairmont Copley Plaza (grande dame on Copley Square). Browse options on Hotels.com Boston or VRBO Boston.

Cape Cod (base: Chatham) + Nantucket Day Trip

Days 3–5: Shingled villages, ocean light, and ferry to cobblestoned Nantucket

• Drive Boston → Chatham: ~2–2.5 hours via Route 3 and the Sagamore Bridge (tolls possible). Consider a stretch at Sandwich Boardwalk or the Heritage Museums & Gardens en route.
• Highlights: Cape Cod National Seashore beaches (Coast Guard Beach, Race Point), Chatham Lighthouse overlook, Provincetown galleries and dune landscapes, antique-hunting along historic Route 6A.
• Cape Cod Rail Trail: Flat, scenic cycling through kettle ponds and cranberry bogs—easy mileage and frequent ice-cream stops.
• Nantucket day trip (from Hyannis): High-speed ferries run ~1 hour; foot-passenger roundtrips typically $80–$110 per adult. Vehicle ferries are limited and pricey—park in Hyannis and walk on. On island: stroll Main Street’s whaling-era homes, Siasconset Bluff walk to Sankaty Head Light, and the Whaling Museum.
• Where to eat (Cape): Chatham Pier Fish Market (lobster rolls with fishing fleet views), Mac’s Shack Wellfleet (pristine sushi and local seafood), Sesuit Harbor Cafe (picnic tables on the water), The Lobster Pot in Provincetown (old-school favorite with bay views). Breakfast at Hangar B (legendary pancakes) or PB Boulangerie (butter-rich kouign-amann).
• Dinner splurge: Twenty-Eight Atlantic at Wequassett (fine dining on Pleasant Bay) or The Sacred Cod at Chatham Bars Inn (New England classics with polish).

Where to stay (4–5 stars): Chatham Bars Inn (resort grandeur by the water), Wequassett Resort & Golf Club (five-star service and bay views), or Ocean Edge Resort & Golf Club (mansions and villas). See Hotels.com Cape Cod and VRBO Cape Cod.

Portland, Maine

Days 6–7: Old Port cobblestones, oyster bars, and lighthouse panoramas

• Drive Chatham → Portland: ~3–3.5 hours (use the Sagamore Bridge → I‑495/I‑95). Stretch your legs in Portsmouth, NH if you’d like a garden walk and coffee.
• Highlights: Portland Head Light at Fort Williams Park (Maine’s most photographed lighthouse), Old Port boutiques and galleries, sunset along the Eastern Promenade, and ferry views of Casco Bay’s calendar of islands.
• Where to eat: Eventide Oyster Co. (brown-butter lobster roll and briny oyster selection), Fore Street (wood-fired local cuisine; book ahead), The Honey Paw (Asian-inspired comfort dishes), Scales (waterfront seafood). For rolls with a lighthouse view, Bite Into Maine’s truck at Fort Williams Park is a local favorite (seasonal).
• Coffee & pastries: Tandem Coffee Roasters (cardamom buns) and Standard Baking Co. (morning buns, baguettes).

Where to stay (4–5 stars): The Press Hotel (stylish nod to its newspaper past), Portland Harbor Hotel (central and refined). Compare options on Hotels.com Portland, Maine and VRBO Portland, Maine.

Camden & Midcoast Maine (Camden, Rockport, Rockland)

Days 8–9: Sail lofts, art museums, and the state’s prettiest harbor

• Drive Portland → Camden: ~1.75–2 hours along US‑1. Detour to Wiscasset for a quick lobster roll at Red’s Eats (expect a line) and river views.
• Highlights: Camden Hills State Park (drive or shuttle to Mount Battie for harbor-and-island vistas), Rockland’s Farnsworth Art Museum (Wyeth family works), and Owls Head Lighthouse.
• Where to eat: McLoons Lobster Shack in South Thomaston (arguably Maine’s best roll, picnic tables overlooking a working harbor), Primo in Rockland (farm-to-table landmark; book early), Long Grain (creative Southeast Asian plates), and Fresh & Co. for waterfront seafood.
• Breakfast & coffee: Boynton-McKay (old apothecary turned brunch icon) and Owl & Turtle Bookshop Café (cozy cappuccinos).

Where to stay (4–5 stars): Camden Harbour Inn (Relais & Châteaux, many rooms with bay views), Whitehall (stylish, porch-forward inn). Explore Hotels.com Camden, Maine or VRBO Camden, Maine.

Bar Harbor & Acadia National Park

Days 10–12: Carriage roads, granite peaks, and wave-lashed cliffs

• Drive Camden → Bar Harbor: ~1.75–2 hours. Arrive via the scenic Route 3 causeway onto Mount Desert Island.
• Acadia essentials: Park Loop Road (Sand Beach, Thunder Hole, Otter Cliffs), easy carriage-road cycling (well-graded crushed stone), Jordan Pond House for popovers with a Penobscot panorama, and Bass Harbor Head Lighthouse at golden hour. Vehicle passes are ~$35 (valid 7 days). Cadillac Mountain’s summit road requires a separate timed reservation—book ahead for sunrise or mid-morning.
• Where to eat: Thurston’s Lobster Pound (Bernard; waterside trays of just-cooked lobster), Beal’s Lobster Pier (Southwest Harbor; crack-your-own classics), Galyn’s (turf-and-surf with harbor views), and Side Street Café (casual comfort; gluten-free friendly).
• Coffee & breakfast: Café This Way (hearty scrambles and blueberry pancakes), Coffee Hound at the pier (espresso before the Park Loop).

Where to stay (4–5 stars): Bar Harbor Inn & Spa (waterfront walking path just outside), Balance Rock Inn (boutique elegance), West Street Hotel (modern rooms; adults-only rooftop pool in season). See Hotels.com Bar Harbor and VRBO Bar Harbor.

Kennebunkport

Day 13: Postcard harbor, Goose Rocks Beach, and a final lobster roll showdown

• Drive Bar Harbor → Kennebunkport: ~3.25–3.75 hours. This sets you up for an easy final hop to Boston.
• Highlights: Ocean Avenue coastal drive past the Bush Compound lookout, the soft sands of Goose Rocks Beach, and galleries in Dock Square.
• Where to eat: The Clam Shack (award-winning lobster rolls in the village center), Earth at Hidden Pond (woodland setting with seasonal plates), and White Barn Inn Restaurant (refined New England tasting menus).
• Coffee & treats: Boulangerie (crusty loaves, morning buns) and Rococo Ice Cream (creative, small-batch flavors).

Where to stay (4–5 stars): White Barn Inn, Auberge Resorts Collection (destination dining), Cape Arundel Inn & Resort (Atlantic views). Browse Hotels.com Kennebunkport or VRBO Kennebunkport.

Boston (Departure)

Day 14: Return to Boston and fly home

• Drive Kennebunkport → Boston: ~1.5–2 hours via I‑95/US‑1. If time allows, detour to Salem for colonial streets and witch-trial history (late September is lively). If you want a guided perspective, consider booking earlier in the trip:
  • Salem Witch Trials Tour from Boston by optional Ferry or Train

    

• Flights: Check current fares and times on Trip.com or Kiwi.com. If you prefer to overnight near the airport, search Hotels.com Boston.

Pacing, foliage, and practical tips

• Driving cadence: All legs are under 4 hours. Expect some traffic around Boston and the Cape bridges on weekends—morning departures help.
• Foliage timing: Northern/coastal Maine often begins turning late September to early October; Boston and the Cape peak later. Your northbound arc positions you to catch early color in Maine, with hints lingering farther south.
• Budgeting: Car rentals ~$60–$120/day in late September; Nantucket high-speed ferry ~$80–$110 RT per adult on foot; Acadia vehicle pass ~$35 (7 days); lobster rolls $22–$38 depending on market price.
• Mobility: Choose short, scenic walks (carriage roads in Acadia; easy lighthouse paths) and use tours in Boston to minimize walking strain.

Suggested 14-day block summary

• Days 1–2: Boston—Freedom Trail, North End food tour, sunset harbor cruise; dine at Neptune Oyster or Row 34.
• Days 3–5: Cape Cod (Chatham base)—National Seashore, Provincetown day, Nantucket ferry, Sesuit Harbor Cafe lobster rolls.
• Days 6–7: Portland—Portland Head Light, Old Port, Eventide Oyster Co., Fore Street.
• Days 8–9: Camden/Midcoast—Mount Battie views, Farnsworth Museum, McLoons Lobster Shack, Primo.
• Days 10–12: Bar Harbor/Acadia—Park Loop Road, carriage roads, Jordan Pond popovers, Thurston’s Lobster Pound.
• Day 13: Kennebunkport—Goose Rocks Beach, The Clam Shack, White Barn Inn.
• Day 14: Return to Boston and depart.

This New England road trip pairs easy coastal drives with deeply satisfying meals—from brown-butter lobster rolls to fine dining with lighthouse views—plus history that shaped a nation. With thoughtful pacing and 4–5‑star stays throughout, you’ll savor the season’s colors at exactly the right speed.