The Ultimate New England Road Trip: A 10-Day Itinerary From a 25-Year Local

The Route That Covers It All

After 25 years of driving New England’s back roads, coast highways, and mountain passes, I have refined this route through dozens of trips — showing it to friends, family, and visitors who want to see the best of the region in a realistic timeframe.

This 10-day loop starts and ends in Boston, covering six states, the Atlantic coast, mountain ranges, college towns, and classic New England villages. You can compress it to 7 days by cutting rest days, or stretch it to 14 by lingering in places you love.

Total driving distance: ~1,100 miles Best time: Late September to mid-October (foliage), June (summer), or late May (value)

Day 1: Boston

Focus: Historic core, waterfront, North End Driving: None (walk or use the T)

Start in Boston. Even if you have been before, give it a full day. Boston is best explored on foot.

Morning: Walk the Freedom Trail from Boston Common through the North End. Do not try to do all 16 stops — focus on the highlights: Old North Church, Paul Revere’s house, Faneuil Hall. The walk itself through cobblestone streets and colonial buildings is the point.

Lunch: Mike’s Pastry in the North End gets the tourist attention, but Modern Pastry next door has better cannoli with shorter lines. For lunch, grab a table at Neptune Oyster (arrive at 11 AM to beat the wait) — their lobster roll is the best in Boston, served warm with butter on a brioche bun.

Afternoon: Walk the Harborwalk along the waterfront from the North End to the Seaport. The Institute of Contemporary Art has a stunning waterfront building and is worth an hour. Or cross the river to Cambridge and walk through Harvard Yard and along Brattle Street.

Evening: Dinner in the South End — Boston’s restaurant row. Myers + Chang (Asian fusion) or Toro (Spanish tapas) are both excellent.

Stay: Boston hotel or Cambridge

Day 2: Boston to Salem to Portland, Maine

Driving: 110 miles, 2.5 hours (plus stops) Focus: Witch trials history, Maine’s food capital

Morning: Drive 30 minutes north to Salem. Skip the cheesy witch museums in town and go straight to the Peabody Essex Museum — one of the best art and culture museums in New England, housed in a stunning building with a transplanted Chinese house inside. Walk the McIntire Historic District for beautiful Federal architecture.

Midday: Drive north on I-95 into Maine. Cross the Piscataqua River Bridge and you are in a different world — the trees get taller, the towns get quieter, the pace slows down.

Afternoon: Arrive in Portland, Maine. Drop bags and walk the Old Port — cobblestone streets lined with independent shops, galleries, and more restaurants per capita than almost any city in America.

Dinner: Portland punches absurdly above its weight for food. Eventide Oyster Co. (their brown butter lobster roll is legendary), Fore Street (wood-fired everything, book ahead), or Duckfat (Belgian fries, paninis, and craft sodas — do not miss the truffle fries).

After dinner: Walk the Eastern Promenade for sunset views over Casco Bay.

Stay: Portland, ME

Day 3: Portland to Acadia National Park

Driving: 160 miles, 3 hours Focus: Coastal Maine, Acadia

Morning: Before leaving Portland, hit the Portland Head Light in Cape Elizabeth — the most photographed lighthouse in America. It is 15 minutes from downtown and worth the detour.

Drive: Take Route 1 north instead of the highway for at least part of the journey. Stop in Camden for the view from Mount Battie (5-minute drive to the summit) — the harbor, islands, and mountains in one panorama. Grab lunch at Cappy’s Chowder House on the wharf.

Afternoon: Arrive at Mount Desert Island and Acadia National Park. Check into your accommodation in Bar Harbor or Southwest Harbor.

Evening: Drive the Park Loop Road (27 miles). Key stops: Sand Beach, Thunder Hole (go at mid-tide for the best effect), Otter Cliff, and Jordan Pond. If timing works, catch sunset from the top of Cadillac Mountain — the first place in the US to see sunrise from October through March, and spectacular at sunset year-round.

Dinner: Jordan Pond House for popovers (a tradition since the 1890s), or Side Street Cafe in Bar Harbor for lobster mac and cheese.

Stay: Bar Harbor or Southwest Harbor, ME

Day 4: Acadia Full Day

Driving: Minimal (within the park) Focus: Hiking, coastline, lobster

Morning: Wake early for sunrise on Cadillac Mountain if you did sunset yesterday (or vice versa). Note: vehicle reservations are required for Cadillac Mountain sunrise from May through October — book well in advance.

Late morning: Hike the Beehive Trail (1.5 miles, moderate) — iron rungs and ladders up a cliff face with ocean views. It sounds intimidating but is manageable for anyone comfortable with heights. Or choose Gorham Mountain Trail for a less exposed alternative with similar views.

Lunch: Drive to Thurston’s Lobster Pound in Bernard (southwest side of the island). Sit on the dock, order a 1.5 lb steamed lobster with corn and coleslaw. This is the real Maine lobster experience — paper plates, plastic bibs, mallets, and the harbor right there.

Afternoon: Bike or drive the carriage roads — 45 miles of broken-stone roads built by John D. Rockefeller Jr. in the early 1900s. They wind through the park’s interior with stone bridges, mountain views, and no cars. Rent bikes in Bar Harbor.

Evening: Walk Bar Harbor’s Main Street. Pop into Geddy’s for a beer, or McKays Public House for chowder. If it is a clear night, drive back up Cadillac Mountain for stargazing — the park has some of the darkest skies on the East Coast.

Stay: Bar Harbor, ME

Day 5: Acadia to White Mountains, New Hampshire

Driving: 180 miles, 3.5 hours Focus: Transition to the mountains

Morning: One last Acadia experience. Take the short walk to Ship Harbor or Wonderland on the quiet side for tide pooling, or drive to Schoodic Point (the only part of Acadia on the mainland) for dramatic wave action on granite.

Drive: Head west through Maine and into New Hampshire. The landscape shifts from coastal to forest to mountains. Stop in Bethel, Maine for lunch if you are hungry — a classic New England town with a good general store.

Afternoon: Arrive in the White Mountains. Check into your hotel or inn in North Conway or Jackson — both are great base camps.

Evening: Drive the Kancamagus Highway (if here during foliage) or explore North Conway’s outlet shopping and restaurants. Moat Mountain Smokehouse has excellent BBQ and craft beer. May Kelly’s is an Irish pub with surprisingly good food.

Stay: North Conway or Jackson, NH

Day 6: White Mountains

Driving: Minimal Focus: Mountains, waterfalls, scenic views

Morning: Hike Franconia Notch. The Franconia Ridge Trail is one of the most spectacular hikes in the Northeast — above treeline with 360-degree views. It is a full-day commitment (8.6 miles, strenuous). For a shorter option, take the Cannon Mountain Aerial Tramway to the summit for views without the sweat.

Alternatively, hike Mount Willard (3.2 miles round trip, easy-moderate) — the reward-to-effort ratio is the best in the White Mountains. The view from the cliff edge over Crawford Notch is jaw-dropping.

Lunch: The Notch Grille at the Notchland Inn, or bring a packed lunch to eat at the overlooks.

Afternoon: Stop at Diana’s Baths (North Conway) — a series of cascading waterfalls and swimming holes that are beautiful in any season. Easy 1.2-mile walk from the parking lot. Or visit the Mount Washington Cog Railway — a steam train to the summit of the highest peak in the Northeast (6,288 feet). The views from the top extend to four states, Quebec, and the Atlantic.

Evening: Dinner at Thompson House Eatery in Jackson — farm-to-table in a converted barn. One of the best restaurants in the mountains.

Stay: White Mountains area

Day 7: White Mountains to Stowe, Vermont

Driving: 120 miles, 2.5 hours Focus: Vermont villages, covered bridges

Morning: Drive west through Vermont. Take Route 2 through St. Johnsbury and the rural heart of Vermont. Stop at the Fairbanks Museum if you are interested in natural history, or just admire the brick downtown.

Late morning: Detour south to Woodstock, VT — consistently ranked the prettiest small town in America. Walk the covered bridge on the edge of town, browse the shops on Central Street, and visit the Billings Farm & Museum to see a working Vermont dairy farm.

Lunch: The Prince and the Pauper in Woodstock for upscale Vermont cuisine, or Mon Vert Cafe for excellent sandwiches and coffee.

Afternoon: Drive north to Stowe via Route 100 — the scenic backbone of Vermont. Stop at the Cold Hollow Cider Mill in Waterbury for free cider samples and their famous cider donuts. If you have time, Ben & Jerry’s factory is right next door (yes, it started here).

Evening: Arrive in Stowe. Walk the village and have dinner at Hen of the Wood — one of the best restaurants in Vermont, using hyper-local ingredients. Book ahead.

Stay: Stowe, VT

Day 8: Stowe to Burlington to Berkshires

Driving: 200 miles, 4 hours Focus: Lake Champlain, college towns, Berkshire culture

Morning: Drive 40 minutes to Burlington, VT. Walk Church Street Marketplace — a pedestrian outdoor mall with street performers, local shops, and restaurants. Walk down to the Burlington Waterfront on Lake Champlain for mountain views across the water.

Brunch: Penny Cluse Cafe is Burlington’s legendary breakfast spot. Gingerbread pancakes, huevos rancheros, the best home fries in Vermont.

Midday: Drive south through the Champlain Valley. This is a long driving day, but the route through central Vermont is beautiful — rolling farmland, red barns, and mountain views the entire way.

Afternoon: Arrive in the Berkshires, western Massachusetts. Check into an inn in Stockbridge, Lenox, or Great Barrington.

Evening: If it is summer, check the Tanglewood schedule — the Boston Symphony Orchestra’s summer home hosts concerts in an open-air venue surrounded by lawns. Pack a picnic. If not concert season, have dinner at The Red Lion Inn in Stockbridge — serving continuously since 1773.

Stay: Berkshires, MA

Day 9: Berkshires to Mystic to Newport

Driving: 150 miles, 3 hours Focus: Connecticut coast, Rhode Island mansions

Morning: Explore the Berkshires. Visit Norman Rockwell Museum in Stockbridge (his actual studio is on the grounds), or hike Monument Mountain (2.6 miles, moderate) — the spot where Hawthorne and Melville famously met during a thunderstorm hike in 1850.

Late morning: Drive east to Mystic, Connecticut. Visit the Mystic Seaport Museum — the nation’s largest maritime museum with historic ships, a recreated 19th-century seaport village, and a working preservation shipyard. Budget 2-3 hours.

Lunch: Mystic Pizza (yes, the one from the Julia Roberts movie). It is actually good pizza and the experience is fun. Or S&P Oyster Company on the harbor for seafood.

Afternoon: Drive to Newport, Rhode Island (1 hour). Walk the Cliff Walk — a 3.5-mile path along the ocean cliffs behind the Gilded Age mansions. The views alternate between crashing surf and absurdly opulent estates. Tour The Breakers (Vanderbilt mansion) if you want to go inside one — it is the most impressive.

Evening: Dinner on Thames Street in Newport’s harbor area. The Black Pearl for chowder, Giusto for Italian, or The Mooring for seafood with harbor views.

Stay: Newport, RI

Day 10: Newport to Cape Cod to Boston

Driving: 150 miles, 3 hours (plus stops) Focus: Cape Cod, homestretch

Morning: Drive across the Newport Bridge and head east to Cape Cod. Cross the Sagamore or Bourne Bridge onto the Cape.

Midday: Choose your Cape Cod experience:

• Provincetown (tip of the Cape): Artist colony, whale watching, dunes, and Commercial Street’s eclectic shops. Drive to Race Point Beach for dramatic ocean views.
• Chatham: Classic Cape Cod village with a lighthouse, a fish pier where you can watch boats unload, and a charming Main Street.
• Wellfleet/Truro: Quieter, more natural. Cape Cod National Seashore beaches are stunning.

Lunch: A lobster roll on the Cape is mandatory. Arnold’s Lobster & Clam Bar in Eastham, The Lobster Pot in Provincetown, or Chatham Fish Pier Market for the freshest possible seafood.

Afternoon: Drive back to Boston (1.5-2 hours from mid-Cape). If you have time, stop in Plymouth to see Plymouth Rock (it is small — manage expectations) and the Mayflower II replica ship.

Evening: Final dinner in Boston. Return to the North End for Italian — Giacomo’s (tiny, no reservations, worth the wait) or Pomodoro (romantic, candlelit, BYOB).

Budget Breakdown

Money-saving tips:

• Book B&Bs and small inns instead of chain hotels — they are often the same price with breakfast included and far more character.
• Lunch at lobster pounds and clam shacks is half the price of sit-down restaurants and often better.
• National park passes ($35) cover Acadia. State park entrance fees are $5-15.
• Foliage season is peak pricing. The same trip in June or late May costs 30-40% less.

Packing Essentials

• Layers. Morning temperatures can be 40°F and afternoons 70°F. A fleece, light jacket, and rain shell cover everything.
• Hiking shoes. You will hike at least 3-4 times on this trip.
• Swimsuit. For beaches (summer), hotel pools, and those moments when a swimming hole is too beautiful to pass.
• Binoculars. For whale watching, Cadillac Mountain, and White Mountain overlooks.
• A cooler. For lobster pounds, farm stands, and roadside fruit. You will want to bring food on drives.

The Bottom Line

This route covers the full spectrum of New England — coastal, mountain, urban, rural, historic, and natural. I have driven versions of it more times than I can count and it never gets old. The key is pacing: do not rush. The best moments on a New England road trip happen when you pull over at an unmarked overlook, take a side road to a village you have never heard of, or sit at a harbor watching lobster boats come in.

New England was built for road trips. The distances are short, the scenery changes every 30 minutes, and every small town has something worth stopping for. Trust the route, be flexible, and enjoy the drive.