Looking for the best day trips from Boston? You don’t have to go far! Whether you’re craving a seaside escape, a day immersed in history, or simply a change of scenery, these easy getaways will take you to some of New England’s most memorable destinations, all within about two hours of Boston.
From coastal towns and beautiful beaches to Gilded Age mansions and historic sites, there’s a day trip here for everyone. Best of all, many can be enjoyed without a car, making it easy to get out of the city and explore more of New England.
About this Guide
As a lifelong New Englander, I’ve spent years exploring New England’s coastal towns, historic communities, and hidden gems. This is my curated list of the best day trips from Boston, based on how easy they are to reach, how much you can realistically experience in a day, and the variety of experiences they offer.
This guide will help you choose the best day trip from Boston based on your interests, schedule, and transportation preferences.
Here’s what you’ll find in this guide:
- My top day trip picks from Boston – a mix of historic towns, coastal villages, Gilded Age mansions, scenic spots, and great places to eat.
- Travel times and transportation options, including easy car-free destinations.
- One-day itinerary ideas to help you make the most of your time.
- Guided tour options for those who prefer not to drive or use public transportation.
- Local tips and recommendations to help you choose the right destination.
- Links to detailed destination guides to help you plan your trip.
Be sure to bookmark this page so you can easily find it when you’re ready to plan your next day trip from Boston – and check back as I continue to add new destinations and recommendations.
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Day Trips at a Glance
| Day Trip | Distance from Boston | Best for… | Car Needed? |
| Salem, MA | ~25 miles | History, culture & witchy fun | No |
| Concord, MA | ~25 miles | Revolutionary War history and literary landmarks | No |
| Gloucester, MA | ~32 miles | Working waterfront, beaches & maritime history | No |
| Rockport, MA | ~36 miles | Art galleries, shops & coastal views | No |
| Ipswich, MA | ~35 miles | Historic estates, beaches & countryside | Yes * |
| Manchester-by-the-Sea, MA | ~25 miles | Quiet beaches & small-town charm | No |
| Essex, MA | ~35 miles | Antiques, fried clams & river views | Yes |
| Newburyport, MA | ~38 miles | Walkable downtown with waterfront park | No |
| Newport, RI | ~70 miles | Gilded Age mansions and cliff walk | Yes * |
| Portland, ME | ~110 miles | Food, craft beer, and exploring the Old Port | Yes * |
- While a car is helpful, there are some highly rated organized tours that will allow you to experience these destinations without a car.
Short on time?
Salem is my pick for the easiest overall day trip without a car, Rockport is perfect for classic coastal New England scenery, Newport is worth the longer trip for mansions and dramatic ocean views and Ipswich is the most under-rated destination.
Where is Cape Cod and the Islands? You may be wondering why Cape Cod, Martha’s Vineyard, and Nantucket are not on this list. While those are all wonderful destinations, I wouldn’t consider them an easy day trip from Boston at all.
Driving distances, summer traffic, and ferry travel turn these destinations into a very long day and rushed experience if attempted in a day. I’ve done it and it was not very enjoyable. I recommend saving these destinations for an overnight or weekend getaway instead.
If you absolutely want to experience a piece of the Cape, then I strongly recommend taking an organized trip to Martha’s Vineyard to eliminate all of the logistics to make your day as stress-free as possible. This highly rated tour will take you from Boston right to the ferry (seasonal) and has an optional tour which I’d recommend. Otherwise, you will need to take public transportation on the island which can be very crowded, confusing and waste time.
Martha’s Vineyard Day Trip with Optional Island Tour
Best Day Trips – 1 Hour or Less
Salem, MA
Best for: History, museums, and a little witchy fun
Travel time from Boston: About 30-45 minutes
Car needed: No
Just a short ride north of Boston, Salem is one of the easiest day trips from Boston.
While Salem is best known for its infamous connection to the 1692 witch trials and its modern-day witchy vibe, there’s so much more to discover here. This historic seaside city offers a great mix of colonial and maritime history, waterfront views, a world-class museum and unique shops, all within a compact, walkable downtown
If you want a day trip that combines history with a touch of witchy magic and a little spooky fun, Salem is hard to beat. Explore its infamous past, wander historic streets, browse local shops and enjoy some waterfront dining, all without needing a car.
Just take the MBTA Commuter Rail from Boston’s North Station and it’s just a 5 minute walk from Salem station to downtown. During the warmer months, you can also take the ferry from Boston for a scenic alternative.
Salem Day Trip Itinerary
Morning: Start in the heart of Salem with a Salem Trolley Tour for a narrated one hour tour through beautiful and historic Salem. From there, explore the historic streets around the Old Town Hall and Essex Street and visit the Witch Trials Memorial.
Afternoon: Head down to Pickering Wharf for waterfront dining, then explore Derby Wharf and the historic harbor. Spend some time at the Peabody Essex Museum before browsing the unique shops along Essex Street. And if you’re feeling curious, stop along the way for an aura reading or psychic reading – You are in Salem after all!
Evening: Before heading back to Boston, enjoy dinner at one of Salem’s historic restaurants – Turners Seafood, The Ledger or Rockafellas.
For more ideas, read How to Have a Wicked Good Day in Salem, MA.
Salem in October
In October, Salem transforms into a Halloween destination filled with witches, costumes, haunted happenings, and plenty of spooky fun.
Insider Tip: If you’re visiting during October, expect significantly larger crowds and allow extra time for attractions and dining. Be sure to read my Tips on How to Survive October and Halloween in Salem, MA.
Prefer a Guided Tour?
Don’t want to take the train or deal with driving and parking? A guided tour from Boston is another easy way to visit Salem. These tours include transportation from Boston, along with a planned itinerary, making this a convenient option if you prefer to leave the logistics to someone else.
- From Boston: Salem Witch Trials History Tour – Leave Boston by Bus/Coach and spend the day in Salem visiting the most popular sites. This includes entry to the Salem Witch Museum, House of Seven Gables and Hocus Pocus House grounds.
- From Boston: Salem & Hammond Castle Private Day Trip – Pair your Salem trip with a tour of a Medieval-style castle in Gloucester, MA.
Getting to Salem, MA
- By Car: ~25 miles | ~ 30-45 minutes
- By Train: MBTA Newburyport/Rockport Line (Salem stop) from Boston’s North Station
- Walk from Station: ~5 minutes to downtown
- Parking: Museum Place Garage or the MBTA Garage
- By Ferry: From late spring through fall, the Salem Ferry offers seasonal service between Boston’s Long Wharf and Salem for about $54 round trip. The ferry terminal is about a 15-minute walk from downtown, making this a scenic and convenient option for a day trip.
Insider Tip: You may be able to get the MBTA Ferry commuter rate ($8.00) Monday-Friday during the commuter rush hour.
When to Visit: October is undoubtedly Salem’s busiest month, but the city is a year-round destination. Spring and winter offer quieter crowds and a more relaxed experience, while summer brings out the waterfront activities and outdoor dining. Fall, especially October, is when Salem really comes alive with all their Haunted Happenings and Halloween festivities. Many popular attractions, including the Salem Witch Museum, Peabody Essex Museum, and shops, are open year-round.
Concord, MA
Best for: History lovers, literary fans, and anyone who enjoys exploring charming New England towns on foot.
Travel time from Boston: About 30–45 minutes
Car needed: No
If you’re looking to explore beyond Boston, Concord is an easy day trip for history lovers. This historic town is home to the site of the “shot heard round the world,” marking the start of the American Revolution. It was also home to some of America’s most celebrated writers, whose homes and final resting places you can explore today.
Concord Center is only a mile away from the MBTA Commuter Rail making it a great destination for a car-free day trip. Just be prepared to do a little walking. Concord’s historic center is compact and walkable, but to see all the major sites in a day you will likely need to cover 4-6 miles.
Concord Day Trip Itinerary
Morning:
Start at the Concord Visitor Center to grab a map and then head to the Concord Museum for an introduction to the town’s Revolutionary War and literary history. Continue to Louisa May Alcott’s Orchard House, the historic house where she wrote her famous novel, Little Women.
Afternoon:
Head back to Concord Center for lunch at the historic Colonial Inn or try Main Street Cafe for something a little more casual. After lunch, head over to Minute Man National Historical Park. Explore the Old North Bridge and The Old Manse, which sit next to each other along the Concord River. If you’re up for more walking, visit Sleepy Hollow Cemetery, home to Authors’ Ridge, where Louisa May Alcott, Ralph Waldo Emerson, Henry David Thoreau, and Nathaniel Hawthorne are buried.
Evening:
Return to Concord Center for an early dinner or drinks at Fiorella’s Cucina before making the 20-minute walk back to the MBTA station for your train to Boston.
Getting to Concord, MA
By Car: ~20 miles | ~35–45 minutes
By Train: MBTA Fitchburg Line (Concord stop) from North Station
Walk from Station: The Concord Visitor Center is about a 20 minute walk (~1-mile) from Concord MBTA Station.
Parking: Concord Visitor Center has free parking behind the building, and additional free lots and metered street parking are available around town.
Cape Ann, MA
Cape Ann is one of my favorite areas of the North Shore and it’s a perfect day trip from Boston. This beautiful coastal region is made up of five towns, each with its own personality and something different to experience.
- Gloucester has a working waterfront, is steeped in maritime history & has a Medieval Castle to explore (Car-free)
- Rockport is known for its famous fishing shack, Motif No. 1 and its art galleries, shops and beautiful coastal views (Car-free)
- Manchester-by-the-Sea is the perfect car-free beach experience with small-town charm (Car-free)
- Ipswich is filled with historic houses along a countryside with a Gilded Age Mansion and stunning white sand beach
- Essex is considered the birthplace of the fried clam and filled with antique shops and views of the Great Marsh
Cape Ann provides so many options for a Day Trip from Boston whether you have a car or not. Since this region is so compact, combining two destinations in a single day trip could be an option depending on what you plan on doing and whether you have a car.
Cape Ann is one of my favorite alternatives to the more crowded Cape Cod, offering working waterfronts, charming villages, beaches, historic estates and some of the North Shore’s most beautiful coastal scenery. Find out why I love Cape Ann in my post: Cape Ann vs Cape Cod: Why I Think Cape Ann Is the Better Choice
Gloucester, MA (Cape Ann)
Best for: Maritime history, authentic working harbor, art and culture
Travel time from Boston: About 50–60 minutes
Car needed: No (unless visiting Hammond Castle)
As America’s oldest seaport, Gloucester is the centerpiece of Cape Ann and offers an authentic taste of a New England working waterfront. Visit Gloucester to experience its bustling harbor, beautiful beaches, stunning coastal landscapes and a vibrant culture scene. Hidden Gem: Don’t miss exploring Hammond Castle, a medieval-style castle built in the 1920’s by inventor John Hays Hammond, Jr.
Getting to Gloucester from Boston takes just about one hour by car or the MBTA commuter rail, making it a great car-free option.
Gloucester Day Trip Itinerary
Morning: Start your day at the spectacular Hammond Castle Museum, a medieval-style castle overlooking the ocean. Since Hammond Castle isn’t within easy walking distance of downtown or the train station, you’ll need a car or guided transportation.
Visiting without a Car? You can still experience Hammond Castle with this guided option which includes transportation to/from the Gloucester MBTA Commuter Rail station plus entry fee to Hammond Castle for a 2 hour visit. Day Trip From Boston: Explore Hammond Castle Museum
Pair your visit to Hammond Castle with a trip to spooky Salem, MA with this tour: From Boston: Salem & Hammond Castle Private Day Trip
Insider Tip: Rideshares can be limited in Gloucester, MA and cell service may be spotty depending on your service provider, especially in the Hammond Castle area.
Afternoon: Head downtown to the working waterfront and Harbor Loop and stroll along Main Street to browse the shops. Enjoy lunch near the waterfront, then explore Gloucester’s maritime history with a walk along Stacy Boulevard to see the Fishermen’s Memorial. If time allows, visit Stage Fort Park for a different perspective of the harbor or take the water shuttle to Rocky Neck Art Colony to visit the galleries and studios.
Evening: Finish with dinner overlooking the harbor at the Seaport Grille or 1606 Restaurant & Oyster Bar inside the Beauport Hotel. If taking the MBTA, try the Azorean Restaurant – it’s directly across from the MBTA station. If you’re staying later, catch some live music at one of Gloucester’s local venues like Minglewood or The Cut but be sure to check the train schedule for the last train.
Getting to Gloucester, MA
- By Car: ~32 miles | ~50–60 minutes
- By Train: MBTA Newburyport/Rockport Line (Gloucester stop) from North Station (Do not get off at West Gloucester) Be sure to get on a train that has a final destination of Rockport (not Newburyport) as the line divides after Beverly.
- Walk from Station: ~10 minutes to downtown
- Parking: St. Peter’s Square parking, downtown municipal parking lots or street parking
When to Visit: May-October is best for warmer weather but Gloucester is a place I visit year-round. Summer is the busiest with all the waterfront action and outdoor dining. Spring and Fall offer cooler temperatures and indoor activities. Winter is the quietest but is worth a visit around the holidays to see the Lobster Trap Christmas Tree all lit up.
How to Spend a Wonderful Winter Weekend on Cape Ann
Insider Tip: Gloucester and Rockport can easily be combined into one Cape Ann day trip if you’re driving. Start in Gloucester and make your way to Rockport for the afternoon to spend the later part of the day to visit Motif No.1 and stroll through Bearskin Neck.
Rockport, MA (Cape Ann)
Best for: Coastal scenery, art galleries, shopping and a classic New England village experience.
Travel time from Boston: About 50-65 minutes
Car needed: No (unless visiting Halibut Point)
If you love charming coastal towns, Rockport is a great day trip from Boston. It‘s the perfect escape where you can spend time wandering around Bearskin Neck, popping into the little galleries and shops, and taking in the harbor views. Of course, there’s that iconic red fishing shack, Motif No. 1, which made the town famous that you won’t want to miss.
Rockport Day Trip Itinerary
Morning: Start the day downtown along 1-T Wharf to explore Rockport’s picturesque waterfront and see Motif No. 1. Then head over to Bearskin Neck to wander through the galleries, shops, and enjoy the waterfront views. At the end, you can walk out on the breakwater for a different perspective.
Afternoon: Enjoy lunch at Roy Moore Lobster Company or Fleur Cuisine Harborside. After lunch, relax at Front Beach, and stop for something sweet at Tuck’s Candy Factory. If you have a car, consider visiting Halibut Point State Park instead for dramatic coastal views and a walk around the former granite quarry.
To learn more about Halibut Point, read Best North Shore Walking Trails That Will Soothe Your Soul
Evening: End your day with dinner in downtown Rockport at The Fish Shack or Feather & Wedge. If you visit Halibut Point, stop at The Lobster Pool, around the corner, to enjoy seafood and sunset views before heading back to Boston.
Getting to Rockport, MA
- By Car: ~36 miles | ~50–65 minutes
- By Train: MBTA Newburyport/Rockport Line (Rockport stop) from North Station. Be sure to get on a train that has a final destination of Rockport (not Newburyport) as the line divides after Beverly.
- Walk from Station: ~10–15 minutes to downtown/Bearskin Neck Rockport Station is located a half mile from downtown Rockport and Bearskin Neck
- Parking: Limited street parking downtown can be challenging during summer and peak times. There is a free shuttle service available from Blue Gate Meadow Park to downtown.
Insider Tip: Cape Ann Transportation Authority (CATA) “Rockport Shuttle” offers free shuttle service Mid-May through mid October from the Blue Gate Meadow Park & Ride Lot (5 Blue Gate Lane) and MBTA Station to downtown Rockport. Parking at the shuttle lot is free.
Ipswich, MA (Cape Ann)
Best for: Historic estates, nature and a quintessential New England countryside experience.
Travel time from Boston: About 50–60 minutes
Car needed: Yes (or organized tour option)
Ipswich, MA is a beautiful rural town known for its well-preserved Puritan-era historic houses with more First Period houses (built before 1725) than any other town in America. It’s also home to one of the country’s oldest continuously operating farms and the spectacular Crane Estate, one of the few remaining intact Gilded Age estates in America.
Discover the Best Things To Do in Ipswich, MA
Visiting Ipswich feels like stepping back in time as you drive through its rural countryside, past horse farms, historic homes, and stone walls. It’s a great day trip from Boston, offering a mix of history, nature, beautiful beaches, and grand mansions all in one place.
While the MBTA Newburyport/Rockport Line from North Station stops in Ipswich, most attractions are not within walking distance so this town is best explored with a car or organized tour\transportation.
Ipswich Day Trip Itinerary
Morning: Start your day off at the spectacular Castle Hill at the Crane Estate. Explore the beautifully landscaped grounds, admire the grand estate, and take in sweeping views of the surrounding marshes and coastline. Castle Hill is one of my favorite places on the North Shore and a must-see when visiting Ipswich. Depending on the season, a parking reservation may be required.
Why You Need to Visit Castle Hill on Crane Estate
Visiting without a Car? You can still experience Castle Hill on Crane Estate with this guided option which includes transportation to/from the Ipswich MBTA station and takes you to Castle Hill at the Crane Estate to tour the mansion as a Guest. From Boston: Guest of the Cranes Guided Tour on Crane Estate. Your Commuter Rail ticket, round-trip transportation from the station, and guided mansion tour are all included.
Afternoon: Enjoy lunch in downtown Ipswich or stop at the iconic Clam Box before choosing your afternoon adventure. Visit Russell Orchards for seasonal fruit picking, cider donuts, and wine or cider, or explore the carriage roads at historic Appleton Farms. Prefer the beach? Spend the afternoon at Crane Beach, where you can relax on the sand, walk through the dunes, and explore the surrounding coastal landscape.
Evening: Finish your day with dinner at the historic 1640 Hart House, one of the oldest surviving structures in America and, according to local lore, possibly haunted. Or head to nearby Essex for its famous fried clams and other local seafood specialties.
Getting to Ipswich, MA
- By Car: ~35 miles | ~50–60 minutes
- By Train: MBTA Newburyport/Rockport Line (Ipswich Stop) from North Station. Most recommended attractions are not within walking distance so you will need a car or organized transportation. Be sure to get on a train that has a final destination of Newburyport (not Rockport) as the line divides after Beverly.
- Parking: Town parking lots and street parking in downtown Ipswich; Parking passes are required to visit Crane Beach and Castle Hill at the Crane Estate.
Insider Tip: During summer months, the Cape Ann Transportation Authority (CATA) “Ipswich Explorer” offers free connection Saturdays and Sundays from the Ipswich MBTA Station to many popular attractions to help you explore Cape Ann without a car.
Manchester-by-the-Sea, MA (Cape Ann)
Best for: A Commuter Beach Day at a quieter coastal town with classic New England charm.
Travel time from Boston: About 40–50 minutes
Car needed: No
Manchester-by-the-Sea is a quintessential New England town known for its beautiful Singing Beach, where the sand is famous for making a “singing” sound. This is a great day trip for an easy summer beach day.
Since parking in Manchester-by-the-Sea is very limited for non-residents most beach-goers and visitors take the MBTA Commuter Rail (Manchester Stop) from North Station and make the 15-minute walk (about 0.5 miles) to the ocean. This makes it a great option for a car-free beach day trip.
Manchester-by-the-Sea Day Trip Itinerary
Morning: Start with coffee or breakfast at the Laughing Gull, conveniently located across from the MBTA station. Take the short walk to Singing Beach and spend the morning relaxing and enjoying one of the North Shore’s most beautiful beaches.
Afternoon: Grab lunch near the beach, then explore Manchester’s charming downtown shops. Treat yourself to ice cream at Captain Dusty’s and take a walk through the historic district to admire the town’s beautiful 18th- and 19th-century homes.
Evening: Stop in at 35 Beach for some casual, upscale dining. Stroll through Masconomo Park to view the quiet waterfront and watch the sunset (60 Beach Street). Be sure to visit the Atlantis Statue at Reed Park close by.
Getting to Manchester-by-the-Sea, MA
By Car: ~35 miles | ~40–50 minutes
By Train: MBTA Newburyport/Rockport Line (Manchester Stop) from North Station. Be sure to get on a train that has a final destination of Rockport (not Newburyport) as the line divides after Beverly.
Walk from Station: ~5 minutes to downtown; ~15 minutes to beach
Parking: Parking in Manchester-by-the-Sea is very restricted and limited for non-residents, especially on weekends. Downtown options include the Town Hall lot (10 Central Street), Masconomo Park (60 Beach Street) and some street parking for short-term parking.
Essex, MA (Cape Ann)
Best for: Laid back coastal visit paired with another Cape Ann destination.
Travel time from Boston: About 45-50 minutes
Car needed: Yes
Essex is a small, quiet town known for its shipbuilding history, antique shops, and its claim as the birthplace of the fried clam. This quaint little town is very laid back and best paired with Ipswich or another Cape Ann stop. We especially like Essex for its great dining options and views of the Great Marsh.
Popular things to do in Essex, MA include:
- Take a Essex River cruise through the Essex River and Great Marsh for beautiful views and a glimpse of the area’s unique landscape.
- Have lunch at the famous Woodman’s of Essex, home of the original fried clam.
- Learn about Essex’s shipbuilding history at the Essex Historical Society & Shipbuilding Museum.
- Explore the Essex River Cultural District, a one-mile, walkable downtown area along Main Street, with antique shops, galleries, restaurants and views of the river.
Getting to Essex, MA
By Car: ~35 miles | ~45–50 minutes
By Train: Essex is not accessible by MBTA public transportation and must be explored by car.
Parking: Free street parking is available on Main Street and most restaurants have parking lots.
Newburyport, MA
Best for: Waterfront park, shopping & a relaxed coastal day.
Travel time from Boston: About 50–60 minutes
Car needed: No
Newburyport is a beautiful coastal city with an upscale vibe located along the Merrimack River. Its compact, walkable downtown is filled with beautifully preserved Federal-style architecture, local shops, cafés and restaurants.
The Waterfront Park is the perfect place to stroll to enjoy the river views or take a harbor cruise. It’s an easy day trip from Boston and one of my favorite places to go for a relaxed day of shopping, strolling, history, and waterfront dining.
Newburyport is the last stop on the Newburyport\Rockport MBTA Commuter Rail Line, with trains taking about 60 minutes from Boston’s North Station.
The Clipper City Rail Trail begins right at the end of the MBTA platform and leads directly to the waterfront and downtown. The walk along the paved path takes about 20 minutes and is quite enjoyable as you view public art along the way.
Newburyport Day Trip Itinerary
Morning: Start the day exploring Market Square and State Street with its unique boutiques, galleries. Browse in Oldies Marketplace, a fun stop for vintage finds and antiques. Visit the Custom House Maritime Museum if you’re interested in local maritime history.
Afternoon: Stop for lunch at Tuscan Sea Grille or Sea Level Oyster Bar for waterfront dining. Walk along the waterfront to take in the views and explore Newburyport’s charming downtown. Head to The Tannery Marketplace to explore more unique boutiques and shops and try a whoopie pie from Chococoa Baking Co. & Cafe. If you have a car, I highly recommend a visit to Plum Island for some beach and coastal scenery year round.
Evening: Have an early dinner at Bar25 or The Poynt. Or try Mission Oak, an old church converted to a dining space offering steaks, seafood and craft cocktails. Grab a gelato at Dolce Freddo and take a final stroll along the waterfront before heading back to Boston.
Insider Tip: If taking the MBTA, be sure to make the 20 minute walk back to the station before dark as there are no lights along the route.
Getting to Newburyport, MA
- By Car: ~38 miles | ~50-60 minutes
- By Train: MBTA Newburyport/Rockport Commuter Rail Line (Newburyport stop) from North Station. Be sure to get on a train that has a final destination of Newburyport (not Rockport) as the line divides after Beverly.
- Walk from station: The station is about 1 mile walk from downtown along the scenic Clipper City Rail Trail.
When to Visit: Spring through fall, although downtown shops, restaurants, and attractions make it a worthwhile year-round getaway.
Best Day Trips – 2 Hours or less
Newport, RI
Best for: Gilded Mansions, dramatic coastline and elegant vibe.
Travel time from Boston: About 1.5 hours
Car needed: Yes (unless taking an organized tour)
Newport RI is one of my favorite places to visit any time of year. It’s an upscale coastal getaway with Gilded Age mansions, a dramatic coastline and the iconic Cliff Walk. It also has plenty of great shopping and dining options along its historic waterfront. While it’s a slightly longer drive from Boston, the sights and experiences make it well worth the trip any time of year.
Best Things To Do in Newport RI in the Springtime
How to Spend a Weekend in Newport’s Winter Wonderland
Newport is about 1.5 hours from Boston by car. While it’s not easily accessible by public transportation, there are several top rated organized day tours.
Visiting without a car or don’t want to drive? You can still experience the best of Newport with an organized tour that includes round-trip transportation from Boston and an expert guide. It’s an easy, hassle-free way to see Newport’s top attractions without worrying about driving, parking, or navigating.
From Boston: Breakers, Marble House & Downtown Newport Small Group Day Trip
From Boston: Newport Mansions Full-Day Trip
You’ll get to see Newport’s best sights, including The Breakers and Marble House, the iconic Cliff Walk, the historic downtown waterfront, and a scenic drive along Ocean Drive.
Newport, RI Day Trip Itinerary
Morning: Begin with a visit to one of Newport’s magnificent Gilded Age mansions, such as The Breakers, then walk a section of the scenic Cliff Walk for beautiful ocean views and a different perspective of the mansions. If you’re driving, continue along Ocean Drive, a scenic 10-mile route lined with coastal estates, beaches, and spectacular viewpoints.
Afternoon: Head downtown for lunch along Thames Street or along the waterfront. Spend the afternoon exploring Newport’s charming shops along Bowen’s Wharf and Bannister’s Wharf and enjoy the lively harbor atmosphere.
Evening: Finish your day with dinner at the historic White Horse Tavern or The Mooring Seafood Kitchen before heading back to Boston.
Getting to Newport, RI
- By Car: ~70 miles | ~1 hour 30 minutes
- Parking: The best parking options include Gateway Visitors Center Parking Lot (23 America’s Cup Avenue) 23 America’s Cup Avenue. The Newport Mansions have parking available for visitors.
Insider Tip: RIPTA (Rhode Island Public Transit Authority) and Discover Newport, offer a free trolley and bus transportation around Newport to popular tourist destinations mid-May through October. If you use this service, you can get validated discounted parking. Be sure to check times and schedules.
Portland, ME
Best for: Great food, craft beer, and coastal Maine
Travel time from Boston: About 1 hour 45 minutes–2 hours
Car needed: Yes (or organization transportation)
Portland is at the edge of what I would consider an easy day trip from Boston given its distance but it’s a great destination. With its historic Old Port, walkable downtown and one of the best food scenes in New England, Portland, ME offers an experience that’s worth the drive.
A Great Girlfriend Getaway in Portland Maine
If you’re a foodie, this is definitely a place you’ll want to visit. The foodie favorites that locals recommend include Eventide Oyster Co., Central Provisions and Duckfat for their famous duck fat-fried Belgian fries.
Beyond the food, Portland is a great place to explore Maine’s coastal character, including Portland Head Light, Maine’s oldest and most iconic lighthouse.
The Amtrak Downeaster stops in Portland, but the Portland Transportation Center is about 1.5 miles from the Old Port and waterfront. It’s roughly a 30–35 minute walk, so you’d need to take a taxi or rideshare to Old Port.
Visiting without a car? If you’d rather skip the train and leave the driving and logistics to someone else, a guided tour is a great option. This tour lets you experience some of the best of Maine’s southern coast, with stops in Portland, Kennebunkport, and Ogunquit.
Boston to Portland Lighthouse & Kennebunkport Small Group Day Tour
Portland, ME Day Trip Itinerary
Morning: Begin your day in historic Old Port at The Holy Donut for a taste of their famous potato donuts or Standard Baking Co. known for their sticky buns and artisanal breads. Take a narrated Trolley Tour to explore Portland’s neighborhoods and visit Portland Head Light, America’s most photographed lighthouse.
Afternoon: Have lunch at Central Provisions or Duckfat. Spend time wandering around Old Port and browse the shops along Commercial Street and Exchange Street. Walk along the Eastern Promenade.
Evening: Have an early dinner along the water front at DiMillo’s On the Water or Dry Dock Portland before heading back to Boston.
Getting to Portland, ME
- By Car: ~110 miles | about 1 hour 45 minutes–2 hours, depending on traffic
- Parking: Cumberland County Parking Garage is a practical option near the Old Port.
How to Choose the Best Day Trip from Boston
With so many great places within easy reach of Boston, the best day trip really depends on what you want to experience. Here are a few of my favorites based on the type of day you’re looking for:
- Best without a car: Salem, Concord, Rockport, and Newburyport are among the easiest day trips to reach by public transportation from Boston.
- Best for history: Salem for its witch-trial history, Maritime past and Peabody Essex Museum; Concord for its combination of American history and literary landmarks; Gloucester for its maritime and fishing history.
- Best coastal escape: Rockport, Gloucester and Newburyport are great choices for ocean views and waterfront walks. Manchester-by-the-Sea is the easiest beach day. All have classic New England charm.
- Best for shopping and strolling: Newburyport, Rockport, Newport and Salem have the best walkable downtowns filled with independent shops, cafés, and restaurants.
- Best for mansions and coastal scenery: Newport is the perfect choice for a day filled with Gilded Age mansions, ocean views, and the famous Cliff Walk. Ipswich is a closer alternative with its Castle Hill on Crane Estate.
- Best for a girlfriend getaway: Newport, Rockport, Portland and Newburyport are especially fun for a relaxed day of sightseeing, shopping, dining, and exploring together.
Whether you’re looking for history, beaches, charming coastal towns, or simply a change of scenery, there’s a Boston day trip to match almost every interest.
Tips for Planning a Day Trip from Boston
- Start early, particularly for summer and weekend trips.
- Check traffic and transportation schedules before you leave, especially for commuter rail and ferry service.
- Make restaurant reservations for popular destinations and weekends.
- Check seasonal hours for museums, historic sites and attractions.
- For coastal destinations, check beach parking rules and fees before you go.
There’s More to New England Than Boston
Boston is an incredible city to explore, but you may want to get out of the city and experience more of what New England has to offer. One of the best things about visiting Boston is that historic towns, charming coastal villages, grand mansions, and lively waterfronts are all just a short trip away. Many can be explored in a single day, making it easy to add a New England adventure to your Boston trip.
Whether you’re visiting Boston for the first time or you’ve lived here for years, these day trips are an easy way to see more of New England in just a day. Choose a town that catches your interest, grab your walking shoes, and set out to discover a new corner of New England.
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