New England in late September is a painter’s palette—maples blushing crimson up north first, oaks shifting to russet farther south. This one-week road trip hits Boston’s revolutionary landmarks, breezy Cape Cod beaches (with a Nantucket dash), Portland’s culinary scene, and the granite-and-spruce drama of Acadia National Park—timed for color and crafted for comfort.

Expect short, scenic drives (max four hours), long views, and plates stacked with lobster rolls, local oysters, and briny chowder. You’ll base in 4–5-star hotels or high-end rentals, with time for slow coffee mornings, lighthouse walks, and harbors at golden hour.

Practical notes: book ferries (Nantucket) and Acadia’s Cadillac Summit Road vehicle reservation in advance (seasonal). Weekdays are calmer than weekends for leaf-peeping. Pack layers: coastal breezes can make a mild afternoon feel crisp once the sun dips.

Boston

Founded in 1630, Boston pairs cobblestones and copper domes with championship sports and lauded universities. Walk the Freedom Trail where revolution once simmered, linger in the Public Garden, then taste your way through the North End—home to cannoli, espresso, and old-country recipes.

Seafood is the city’s heartbeat: half-shells in the Seaport, buttery lobster rolls near the harbor, and dayboat specials chalked on tavern boards. In fall, Boston’s tree-lined squares glow—especially Beacon Hill’s gaslit lanes at dusk.

• Where to stay (search): VRBO Boston | Hotels.com Boston
• Fly in from Seattle: Search fares on Trip.com or Kiwi.com (SEA–BOS nonstop or 1-stop, ~5.5–7.5 hours, often $250–$500 roundtrip in late September).

Day 1: Arrive Boston, Harbor Welcome, North End Flavors

Morning: Fly SEA → BOS. Pick a mid-morning departure for an afternoon arrival. If you prefer an easy start, request hotel early check-in (many top properties can accommodate with notice).

Afternoon: Check in and stretch your legs with a gentle loop through the Public Garden and along Commonwealth Avenue Mall. Coffee pick-me-up at Tatte Bakery & Café (almond croissants) or Flour Bakery (sticky buns) before a stroll on Charles Street’s boutiques.

Evening: Join a flavorful walk through the North End. Consider the Boston North End Food Tour of 6+ Tastings, Cannoli, Lobster Roll.

Expect artisan salumi, arancini, and a petite lobster roll—plus the story of Boston’s “Little Italy.” After, compare cannoli at Modern Pastry vs. Mike’s Pastry and toast with a Negroni at Caffè Vittoria.

Day 2: Boston Icons by Trolley, Freedom Trail, Sunset on the Water

Morning: Grab breakfast at The Friendly Toast (playful diner classics) or Café Nero (smooth Italian-style espresso). Then circle the city on the Boston Hop-On Hop-Off Trolley Tour with 13 Stops for an easy overview and flexible stops—Copley Square, Boston Common, and the Seaport included.

Afternoon: Walk history with the Freedom Trail History Small Group Walking Tour—from the Old State House to Faneuil Hall, your guide threads the Revolution’s big moments through everyday streets.

Lunch nearby at Neptune Oyster (buttery lobster roll, hot with drawn butter) or Pauli’s (overflowing “Lobstah Roll”).

Evening: Sail into the golden hour on the Boston Harbor Sunset Cruise—watch the skyline glow as you pass Castle Island and the Harbor Islands.

Dinner at Row 34 (raw bar, warm buttered lobster roll) or Mooncusser (seafood-forward tasting menu). Nightcap at The Last Hurrah—whiskey list fit for a historian.

Chatham (Cape Cod)

Cape Cod’s lower-cape town of Chatham is a postcard—shingled cottages, a stately lighthouse, seals in the surf, and hydrangeas nodding in the salt air. It’s a perfect base for quiet beaches, cranberry bog drives, and a quick ferry hop to Nantucket.

Seafood shacks stand shoulder to shoulder with white-tablecloth dining. Late September keeps summer warmth with fewer crowds; sunset skies over Nantucket Sound can stop time.

• Where to stay (search): VRBO Chatham | Hotels.com Chatham

Day 3: Boston → Chatham (2–2.5 hrs), Lighthouse Beach, Classic Cape Dinner

Morning: Pick up your rental car and depart Boston after rush hour. The Sagamore Bridge ushers you onto the Cape; pause at the Sandwich Boardwalk if you fancy a short stroll.

Afternoon: Check in, then wander Chatham’s Main Street—bookshops, galleries, and ice cream windows. Walk to Chatham Lighthouse Beach; keep an eye for seals near the sandbars.

Evening: Dinner at The Impudent Oyster (dayboat scallops; lively bistro vibe) or Del Mar Bar & Bistro (wood-grilled local fish). For a lobster roll with harbor views, Mac’s Chatham Fish & Lobster hits the spot. Nightcap by the firepit if your resort offers it.

Day 4: Nantucket Day Trip (Fast Ferry), Sconset Bluff Walk, Cape Sunset

Morning: Early breakfast at Hangar B Eatery (Chatham Airport—legendary pancakes) or Snowy Owl Coffee Roasters. Drive ~35 minutes to Hyannis for the fast ferry to Nantucket (~1 hr; reserve ahead). On arrival, explore the cobblestone core and Brant Point Lighthouse.

Afternoon: Lunch at The Lobster Trap (warm roll, butter gloss) or Something Natural (bakery sandwiches) if you want a lighter seaside picnic. Walk the Sconset Bluff Walk—rose-covered cottages, endless Atlantic—and, time allowing, pop into Cisco Brewers for a casual flight.

Evening: Ferry back to Hyannis and return to Chatham. Grab a classic lobster roll at Sesuit Harbor Cafe (Dennis; often open into October) or head to The Raw Bar at Popponesset for their famously overflowing version. Stargazing on the beach if skies are clear.

Portland, Maine

Portland is New England’s small-city gourmand—dock-to-dish seafood, James Beard chefs, brick warehouses reborn as bistros, and lighthouses that have inspired painters for generations. It’s compact, walkable, and delicious.

Fall paints the city’s parks and the Western Prom with amber and gold. The Old Port’s cobbles lead to bakeries by morning and cocktail dens by night; bring an appetite.

• Where to stay (search): VRBO Portland | Hotels.com Portland

Day 5: Chatham → Portland (3–3.5 hrs), Lighthouses, James Beard Dinner

Morning: Depart after breakfast to miss bridge traffic. Arrival lunch at Eventide Oyster Co. (brown-butter lobster roll on a pillowy bun) or The Highroller Lobster Co. (creative takes; lobster grilled cheese).

Afternoon: Walk the Old Port, then drive 15 minutes to Portland Head Light at Fort Williams Park—New England’s most photographed lighthouse. Stroll cliffside paths with surf breaking below.

Evening: Dinner at Fore Street (wood-fired, farm-and-sea menu) or Scales (waterfront seafood house). For a postprandial tipple, Blyth & Burrows crafts elegant, maritime-tinged cocktails.

Bar Harbor & Acadia National Park

Mount Desert Island is a tapestry of pink granite, evergreen scent, and ocean mist. Acadia National Park weaves carriage roads, rocky headlands, and quiet ponds into a landscape that glows with early fall color by late September.

Bar Harbor mixes galleries with lobster pounds and schooner masts. Days here start with blueberry pancakes and end under incredible starlight—Acadia is a Dark Sky treasure.

• Where to stay (search): VRBO Bar Harbor | Hotels.com Bar Harbor

Day 6: Portland → Bar Harbor (3–3.5 hrs), Park Loop Road, Jordan Pond

Morning: Start with Tandem Coffee or Standard Baking Co. (morning buns), then drive north via I‑295/ME‑3. Check into your Bar Harbor hotel and head straight into Acadia.

Afternoon: Drive the Park Loop Road: Sand Beach (walk the crescent), Thunder Hole (best with a mid-tide swell), and Otter Cliffs. Take the easy Ocean Path for wave-sculpted granite and spruce perfumes. Late-afternoon tea and popovers at Jordan Pond House with The Bubbles reflected in the water.

Evening: Casual feast at The Travelin’ Lobster (meaty steamed lobsters; excellent rolls) or Galyn’s (white-tablecloth seafood in town). Stargazing along the Shore Path if the sky is clear.

Day 7: Cadillac Summit, Lobster Lunch, Short Flight to Boston

Morning: If you’re game, catch sunrise from Cadillac Mountain (vehicle reservation required in-season; book ahead). Alternatively, walk part of the Carriage Roads or the easy loop around Jordan Pond for peak serenity.

Afternoon: Early lobster roll lunch at Thurston’s Lobster Pound (Bernard; typically open through mid-October). Then it’s a short drive (~20 minutes) to Hancock County–Bar Harbor Airport (BHB) for a seasonal nonstop to Boston (about 1h15–1h25). Search options on Trip.com or Kiwi.com (typical late-September fares ~$130–$250 pp). Connect to your afternoon/evening BOS → SEA flight.

Evening: If your schedule allows a Boston layover dinner, Row 34 and Legal Sea Foods (Logan locations) offer one more taste of New England seafood before the flight home.

Optional Boston Add‑Ons (If You Have Extra Time)

Baseball fans can step inside history with the Tour of Historic Fenway Park.

Or, for a different lens on the harbor, the City Cruises Boston Historic Sightseeing Harbor Cruise adds a narrated, history-rich hour on the water.

Dining cheat sheet (lobster rolls to remember): Neptune Oyster and Pauli’s (Boston); Sesuit Harbor Cafe and The Raw Bar (Cape Cod); Eventide and The Highroller (Portland); Travelin’ Lobster and Thurston’s (Bar Harbor). Each spot is beloved for sweet, fresh meat and the right balance of butter, lemon, and toasted bun.

Logistics recap: All drives remain under four hours. The final Bar Harbor → Boston stretch is replaced with a short flight to keep the pace easy and maximize Acadia time. Book ferries and Acadia’s Cadillac Mountain access in advance for smooth sailing.

In one week, you’ll taste the coast, walk through history, and watch the leaves catch fire from Boston to Acadia. It’s a graceful, good-eating road trip—designed for comfort, color, and that perfect lobster roll by the sea.