Portland to Boston Coastal Drive: York, Ogunquit & Salem

Trip Snapshot:

• Distance & Drive Time: ~115 miles one-way from Portland, ME to Boston, MA. Direct on I-95 takes about 2 hours, but a leisurely coastal meander can stretch 3+ hours (not counting stops). Consider a full day with stops, or an overnight with time to explore Boston.
• Best Time of Year: Late spring through fall for the best mix of beach weather and sightseeing. Summer offers beach days (expect more traffic), while autumn brings crisp weather ideal for city walking (plus Salem’s spooky fall events). Avoid Friday afternoons in summer or holiday weekends unless you love traffic.
• Ideal For: Travelers wanting to experience New England’s variety quaint beach towns, historic sites, and a big city all in one trip. Great for history buffs (Boston and Salem), families (beaches and attractions along the way), and anyone flying out of Boston who wants to turn the trip into a scenic adventure.
• Route Summary: From Portland, head south on I-95 (Maine Turnpike). For a scenic coastal route, hop off at exits for York or Ogunquit to drive along Route 1A/1 through the beach towns of Southern Maine (York, Ogunquit, Wells) and the Kennebunks. Continue into New Hampshire via coastal Route 1B/1A through Portsmouth, then rejoin I-95 over the Piscataqua River. In Massachusetts, you can detour to Salem via Route 1A/114 or stay on I-95/Route 1 straight into Boston.
• Top Highlights: The Nubble Lighthouse at Cape Neddick (York), the Marginal Way footpath in Ogunquit, charming Kennebunkport village (and a glimpse of the Bush family’s Walker’s Point), historic downtown Portsmouth, NH, the witch trial history of Salem, MA, and finally the countless attractions of Boston (Freedom Trail, Faneuil Hall, Fenway Park, and more).

Route Overview

Cape Neddick “Nubble” Lighthouse in York, Maine an iconic stop on the coastal route from Portland to Boston.
This road trip showcases how connected New England’s treasures are. Start by cruising out of Portland on I-95 South, but don’t blink the Maine Turnpike’s first 40 miles are mostly wooded highway until you approach the York exits. To savor the scenery, exit near York (around mile 7 in Maine) and follow signs for Nubble Light/Cape Neddick. Soon you’ll be on Shore Road (Route 1A), where the salty ocean air greets you. In York Beach, make the short detour to Sohier Park here, just offshore on a rocky islet, stands Nubble Lighthouse, perhaps Maine’s most photographed lighthouse. After admiring the red-roofed keeper’s cottage and crashing waves (and maybe grabbing taffy or a doughnut at The Goldenrod in York Beach), continue south on Route 1A. Next up is Ogunquit, a lovely seaside town with a long sandy beach. Park and stroll the Marginal Way, a mile-long cliff walk with sweeping ocean views and benches to linger (the path connects Ogunquit’s downtown to quaint Perkins Cove). Back in the car, you can cruise through Wells (with marshes and antique shops along Route 1) toward Kennebunkport. Turn off at Kennebunk’s Port Road to visit this upscale village browse Dock Square’s boutiques and galleries, or drive out Ocean Avenue for a glimpse of Walker’s Point, the summer home of former U.S. President George H.W. Bush (you’ll see the flagpole and compound on a promontory; there’s a scenic overlook to stop safely). From the Kennebunks, rejoin Route 1 or hop back on I-95 for a quicker jaunt into New Hampshire. You’ll cross the Piscataqua River into Portsmouth, NH, a historic port city. If time permits, take exit 7 and loop through Portsmouth’s charming downtown the red-brick sidewalks, Prescott Park gardens on the waterfront, and myriad restaurants make it a great lunch stop. Finally, crossing into Massachusetts, I-95 bypasses some coastal areas for an extra dose of history, you could detour east to Salem (via Route 1A/114) to immerse yourself in Colonial and witch trial lore. Otherwise, continue on I-95 (which becomes Route 128 around Boston) or Route 1 (more roadside shopping plazas) straight into Boston. As you approach the city on I-93/Route 1, the skyline rises ahead. You’ve gone from Portland’s rocky shores to Beantown’s urban streets, all in a single day’s journey.

Top Stops & Experiences

• Cape Neddick “Nubble” Lighthouse (York, ME): A must-stop for lighthouse lovers. Park at Sohier Park (free) and enjoy the view of this 1879 lighthouse perched on its little “nubble” island just off the coast. In summer, you might see fishermen casting off the rocks and divers exploring below. There’s a small on-site gift shop (seasonal) and often an ice cream truck. It’s an easy stop just 5 minutes off Route 1, and truly a photographer’s dream on a clear day with blue skies, the white lighthouse against the ocean is stunning.
• Ogunquit, ME Beach & Marginal Way: Stretch your legs in Ogunquit (“beautiful place by the sea” in Abenaki). The Marginal Way is a paved footpath that hugs the rocky coastline for just over a mile. Park in town or near Perkins Cove and walk either direction you’ll pass pocket coves, tidal pools, and see artists painting en plein air. Perkins Cove has footbridges, lobster boats, and local eateries (a good spot for chowder or lobster rolls). If it’s a hot day, Ogunquit Beach’s soft sands are perfect for a dip (just be ready for cold Atlantic water!).
• Kennebunkport, ME: This postcard-perfect town is worth a detour. Walk through Dock Square to see its many shops (from souvenirs to fine art). A classic stop is The Clam Shack on the bridge for a lobster roll or fried clams. Drive out Ocean Avenue along the Kennebunk River the road will give you views of some impressive seaside homes. About 2 miles out, pull over at the Walker’s Point overlook, marked by an anchor and American flag, to view the Bush family compound across the water. The rocky coastline here, with waves splashing, is quintessential Maine. Tip: Traffic can be tight through Kennebunkport in summer; patience is key, or visit early in the day.
• Portsmouth, NH: A small city with big history. If you stop downtown, head to Market Square the heart of Portsmouth where you can see the landmark North Church steeple and grab a coffee or craft beer. Stroll the Strawbery Banke Museum area (a preserved neighborhood of 18th-century homes; even if the museum is closed, the exterior vibe is charming). Prescott Park along the river offers gardens and sometimes outdoor concerts. Portsmouth is also known for its dining scene consider lunch at a pub in an old brick building or fresh seafood on the decks by the river. And if you need a quick detour before Massachusetts, the Portsmouth Harbor Lighthouse in nearby New Castle is a short drive and offers scenic views of the harbor and forts.
• Salem, MA (optional): Famous for the 1692 witch trials, Salem provides a change of pace as you near Boston. Park near downtown and explore on foot: the Salem Witch Museum or Witch Dungeon Museum give insights into the hysteria of 1692. Wander Derby Wharf to see the Friendship (a replica tall ship) and the House of the Seven Gables (inspiration for Nathaniel Hawthorne’s novel). Salem’s streets blend colonial history with kitschy witch-themed shops especially fun in October when Halloween events take over. It’s a bit out of the way (you’ll exit I-95 for Route 128/114), but can be a rewarding stop for history and spooky lore buffs.
• Boston, MA: Ending in Boston opens up a world of possibilities. After the serene coastal towns, Boston’s energy is invigorating. Top attractions include walking the Freedom Trail, a red-brick line connecting 16 historical sites like the Old North Church and Paul Revere’s House (you’ve been tracing early American history all day, and here it culminates). Check out Faneuil Hall Marketplace for food and street performers, visit the New England Aquarium on the waterfront, or tour Fenway Park if you’re a baseball fan. Driving in Boston can be challenging with its twisty old streets, so once you arrive, it might be best to park the car (in a garage or at your hotel) and explore by foot or public transit (“The T”). If you’re only here for a short visit, a trolley tour can be a convenient way to see the city’s highlights without getting lost. Note: If you need to drop off your rental car, many agencies have downtown locations consider ending your driving portion upon entering the city to avoid hefty parking fees.

Where to Eat & Stay

• Eat: Along the drive down, seafood is the star. In Maine, you have classics like Fox’s Lobster House by Nubble Light for oceanfront dining, or Barnacle Billy’s in Perkins Cove (Ogunquit) for chowder and rum punch on the deck. Portsmouth boasts farm-to-table spots and cafes; try Portsmouth Brewery for pub fare or Row 34 for oysters. Once in Boston, the culinary options are endless: enjoy Italian in the North End (perhaps at Giacomo’s or Mike’s Pastry for cannoli afterward), or fresh seafood at Legal Sea Foods by Long Wharf. For a quick bite, Quincy Market at Faneuil Hall has dozens of vendors where you can sample New England clam chowder in a bread bowl or a famous Boston cream pie.
• Stay: If you’re making this a multi-day trip, you have choices. Portsmouth, NH makes a great midway overnight stop boutique hotels like The Hotel Portsmouth or big brands like Sheraton Harborside offer comfort steps from downtown. In Boston, staying in the city center lets you experience the nightlife and historic atmosphere: consider lodging in Back Bay or Downtown near the attractions. Big-name hotels (Marriott, Westin, etc.) cluster around Copley Square and the Waterfront. For charm, a B&B in the South End or a historic inn in Beacon Hill (like The Liberty Hotel, a luxe hotel in a converted city jail) can be memorable. Keep in mind Boston hotels can be pricey; if you’re on a budget, staying just outside the city (Cambridge, or along the subway lines) might offer better rates. If your journey is one-way ending in Boston, choose a hotel where you can easily return the rental car nearby or one that’s walking distance to sights so you don’t need to drive further.

Practical Tips

• Traffic Alerts: This route traverses some of New England’s busiest summer areas. If traveling July–August or on weekends, plan for heavy traffic leaving Maine (southbound) especially on Sunday afternoons, and heading into Boston on weekday evenings. To avoid headaches, depart early in the morning from Portland. Likewise, if returning to Maine, try to leave Boston before 3 PM or after 7 PM to dodge weekday rush hour on I-95.
• Tolls: Be prepared for tolls on I-95 (Maine Turnpike toll between York and Kittery, plus the turnpike tolls in New Hampshire). Having about $5–10 in cash is wise if your rental car doesn’t have an E-ZPass. Maine’s toll is around $4, and NH’s Hampton toll around $2 cash lanes are available (or you’ll be billed by plate if no E-ZPass, which can incur rental surcharges).
• Parking in Boston: Driving into downtown Boston is doable but parking is expensive and sometimes hard to find. It’s often easiest to head straight for a parking garage near your first attraction or your hotel. Expect to pay $20–$40 for day parking in central areas. An alternative: park at a MBTA “T” Station on the outskirts (like Alewife Station on the Red Line or Riverside on the Green Line) and take the subway in for a day of sightseeing, to avoid city driving. If your hotel is in the suburbs or Cambridge, utilize rideshares or the T to reach downtown. Boston is wonderfully walkable once you’re in the historic core.
• Beach Weather & Timing: If your goal is beach time in Ogunquit or Kennebunk, note that on hot summer weekends those areas fill up fast. Ogunquit Beach parking can be full by late morning. Plan a beach stop early in the day or later in the afternoon when crowds thin. Also, Maine’s ocean water stays chilly (peaking around 60°F in mid-summer) refreshing but brisk! Have towels and maybe a change of clothes handy in the car.
• Mix & Match: This route is flexible. Short on time? Skip Salem and head straight to Boston on I-95. More time to explore? Add stops like Halibut Point State Park in Rockport, MA (gorgeous coastal views) or the Newburyport, MA waterfront for another quaint town. If you have an extra day, you could spend a night in Boston and then continue south to see Cape Cod or Plymouth. The beauty of having a car is you can tailor the journey to your interests.
• Crossing State Lines: You’ll be zipping through three states (Maine, New Hampshire, Massachusetts) in one day pretty common in New England! Keep an eye on road signs as each state’s route numbers can be confusing (e.g., Route 1 vs 1A). Generally, I-95 will guide you well. Once you hit Massachusetts, you might hear locals refer to I-95/128 and I-93 these are the major highways circling and entering Boston. Don’t be alarmed by the aggressive lane changes Boston drivers have a reputation. Stay calm and use your GPS, and you’ll do fine.
• Outlet Shopping: Just over the border in Kittery, Maine (right before New Hampshire) you’ll see Kittery Premium Outlets along Route 1. If shopping is on your agenda, this is a popular stop for deals on clothing and gear (plus Kittery Trading Post for outdoorsy folks). New Hampshire also offers tax-free shopping, so places like the Mall at Fox Run in Portsmouth or the outlets might tempt you. Just remember to leave space in your luggage!

Rentals & Logistics

This trip is as much about the journey as the destination, and a car gives you ultimate freedom. Many travelers do this route as a one-way rental, picking up a car in Portland and dropping off in Boston check with your rental company about one-way drop fees (our Portland partners often allow Boston drop-off at reasonable rates). If you’re returning to Portland, you can take the faster interstate on the way back after your coastal tour. One logistical tip: if you plan to finish in Boston and you’re not used to city driving, consider returning your rental upon arrival in Boston (to save on parking costs and stress), then use public transport or walking to explore the city. You can always rent another car if you depart Boston for further road trips. Reserve your rental car in advance during peak travel seasons, and inquire about E-ZPass transponders for toll convenience. With your car, camera, and this itinerary in hand, you’re set to experience the quintessential New England trifecta rocky coasts, mountain magic, and urban history all in one epic road trip. Enjoy the ride!