Wicked Summer Fun Guide

Wicked Summer Fun Guide

Wicked Summer Fun Guide

With warmer weather finally here, it has all all dreaming of road tripping. How lucky are we to live in New England, and be able to hop in the car and go to the mountains, the ocean, lakes or fun cities, all on a tank of gas? The options seem endless. Like a Cheese Cake Factory menu, the numerous choices can make it difficult to decide.  What are the best road trips from Boston? With the help of Time Out Boston, Roadtrippers, and my own experience, here are 19 fun places to road trip from Boston.

Keep in mind, some of these spots can be day trips. Some of these require at least an over night stay. Most of these places you can get to and back on a tank of gas, but some require a tank to get there. As always, it’s best to plan ahead, at least a little. If you love a spontaneous road trip, make it a day trip. But if  you plan ahead, you can find somewhere to stay the night, eat, visit attractions, and get the most out of your time and money. Check out these 19 fun places to road trip from Boston.

In no particular order…

  • 1. Provincetown, MA

    116 miles from Boston

    Phenomemanl food, lots of good people watching, shopping, sunsets and art. P-Town is at the very tip of Cape Cod. Traffic can be challenging but it’s a very easy and fun ferry ride from Boston. Sunset at Race Point is spectacular and the Pilgrim Monument is so interesting and the grounds are beautiful. See a show, visit a gallery and shop until your heart’s content. So many great restuarants with views.

    Events & Fun Things to Do in Provincetown Cape Cod

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  • 2. Portland, ME

    112 miles from Boston

    According to Time Out, “the food scene lives up to the hype” in Portland, ME. It’s only about a 2 hour ride to the charming cobblestone streets of downtown Portland. This is the biggest city in Maine and it is chock full of things to see and do. Shopping in the Old Port District, art in the West End, with galleries, live theater and music. The city is very bicycle friendly and they have a popular bike share program. It’s an easy ride from the city to the coast. Don’t forget to get your lobster fix, when in Maine.

    Visit Portland Maine | Travel Planning | Tourism Information

    Explore the land of lighthouses and lobster along the rocky coast of Southern Maine. History, art, tours, and outdoor adventures await. Plan your trip today.

  • 3. Newport, RI

    71 miles from Boston

    Such an easy and quick ride from Boston to beautiful downtown Newport, RI. Home to the Newport Mansions (of the Guilded Age), a stunning coastline which can be viewed on foot along the Cliff walk, pretty parks and much more. There’s no shortage of shopping, restaurants, nightlife and yahts to see. But it’s all about the coastline and mansions, here. All in just a little over an hour’s ride.

    Discover Newport | Official Site for Newport, Rhode Island

    Plan your visit to Newport, Rhode Island and our nearby coastal communities! As the official tourism resource, we'll help you find fun things to do, hotels, events, restaurants, and trip planning information. Whether you're traveling for vacation or business, we have plenty to offer for everyone.

  • 4. Mystic, CT

    98 miles from Boston 

    This old timey New England ship- building seaport town looks like something out of a movie, with it’s quaint little village filled with adorable mom and pop shops. You can take a sunset cruise, visit the world-famous Mystic Aquarium, and like the movie, Mystic Pizza, there is delicious pizza to be found.

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  • 5. Wolfboro, NH

    104 miles from Boston 

    You’ll find “America’s First Resort Town” only about 2 hours from Boston. Wolfboro is on Lake Winnipesaukee, so there is plenty to do on the water and around the water. And there’s plenty to do in the town center, on Main Street. Great shops and food.  Roadtrippers suggest Rattlesnake Island, which they call “a local gem—known for its shape, not snake sightings—and is a scenic spot for day hikes.”

    Visit Wolfeboro

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  • 6. Saratoga Springs, NY

    199 miles from Boston

    In just a smidge over 3 hours, you can be in magnificent Saratoga Springs, NY.  Saratoga Springs is famous for it’s horse track and races (running July 13 through Labor Day). But there is so much more! I visited here right after race season, when it’s a lot quieter, but still fun, with plenty to do. They have a fabulous outdoor music venue, SPAC, or Saratoga Performing Arts Center. There’s Saratoga Lake, top notch dining, and the Roosevelt Salt Baths and Spa which is historic and wonderfully relaxing.

    Visit Saratoga! Travel Guide to Saratoga Springs NY

    See Saratoga like a local with this guide to Saratoga County and Saratoga Springs NY. Discover a thriving restaurant, nightlife and arts scene, plus historic Saratoga Race Course and other hotspots.

  • 7. Kennebunkport, ME

    90 miles from Boston

    In just about an hour and a half (on a good day), you can be transported to this exceptional and quintessential New England town. Kennebunkport is on the coast in southern Maine. It’s well known for it’s impressive beaches like Goose Rocks Beach and Arundel.  They have a Seashore Trolley Museum with a huge collection of streetcars. Of course it’s famous for it’s fresh, local seafood, and many of the locals will tell you to get your lobster rolls at the unassuming Clam Shack, but anywhere you go here, you can’t go wrong. I loved staying in the Kennebunk Inn and walking right into town from there.

  • 8. Block Island, RI

    81 miles from Boston to Naragansett

    71 miles from Boston to Newport

    Take the Ferry from either of these places, it’s only 30 to an hour

    Block Island is so walkable and bikeable. So, once you get off the ferry, you don’t need a car. Many of the most popular attractions and beaches are easily walkable from the ferry dock. If you do want to bring a car, you need to take the ferry from Port Judith (Naragansett) and you will need a reservation. Once you are there, beach it!, Walk, shop, eat, see art , live music and ride a horse. The island has 2 lighthouses, an animal farm for the kids and much more.

    Block Island Tourism Guide & Places to Stay - Visit Rhode Island

    Visit Rhode Island is the #1 trusted place to go for tourism guides and the best places to stay on Block Island RI. Rhode Island has many events and accommodations for you and your family.


  • 9. Martha's Vineyard, MA

    72 miles from Boston to Falmouth – 35 minute ferry ride to Oak Bluffs 
    75 miles from Boston to Woods Hole- 45 minute ferry ride to Oak Bluffs 

    There’s so much to see, and so many different experiences from one island town to the next, on Martha’s Vineyard. Oak Bluffs is a fun town, with an historic carousel, America’s oldest operation platform carousel. There are rows and rows of colorfully painted historic gingerbread cottages, a Tabernacle that hosts a variety of events from live music to Illumination night with Japanese lanterns. There are so many little restaurants, shops and things to see and do on Circuit Ave. You can literally bike all over the island on bike paths. Make sure you visit the lighthouses, and the clay cliffs of Aquinnah.


    Martha's Vineyard Chamber of Commerce helps you make travel plans, find the best hotel or rental, restaurants, businesses & more!

  • 10. Salem, MA

    25 miles from Boston 

    Yes, it’s know for it’s infamous witch trials, but Salem is a specatular place to visit. There is rich history here, beyond the witches, it’s the birthplace of author Nathaniel Hawthorne, who wrote of The House of the Seven Gables. Be sure and tour the 350 year old mansion, Turner-Ingersoll, that was supposedly the house he wrote about. The town is bustling with food, shopping and art. And Time Out recommends you visit , Pioneer Village—”nestled between the woods and the ocean, a ten minute drive from downtown, in Forest River Park—reenacts early 17th century colonial life.”

    Destination Salem | Official Travel & Tourism Website of Salem, MA

    Let Destination Salem be your guide to exploring the city of Salem, MA. Experience Salem art, culture, unique shops & boutiques, and delicious fine dining. Dive into Salem's Witch Trials, maritime, architecture, and literary history and explore museums and a National Heritage Site.

  • 11. Burlington, VT

    216 miles from Boston

    It’s a little over a 3 hour car ride, from Boston, but so well worth it. A road trip to Burlington, Vermont will land you on the eastern shore of Lake Champlain, and just south of the Canadian border. Downtown is happening. Shops and restaurants line Church St. Marketplace, which is for pedestrians only. This vibrant, small city is home to the historic site of Ethan Allen’s Homestead Museum. Burlington is often listed as one of the best places to live in the U.S. It’s home to the University of Vermont. In neighboring South Burlinton, you will find the headquarters of Ben & Jerry’s Ice Cream, which you can tour. The Flynn Center for the Performing Arts and the Burlington Waterfront Park are popular attractions, too.

    Hello Burlington, VT: Things to Do, Places to Stay, Events & More

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  • 12. New York, NY

    215 miles from Boston

    If you can avoid traffic, you can drive to New York City, one of the greatest cities on the planet, in about 3 1/2 hours. But, good luck with that. It’s worth it though. The night life, the culture, the history, some of the top restaurants in the world are here, as well as fantastic museums. The home of Broadway never disappoints. Visit the statue of liberty, do the Brooklyn Bridge, the Empire State building. Take in a show, eat, drink shop in the city the never sleeps. See the 911 Memorial, and look for famous people walking through Central Park.

    New York City Visitor Information - Visit New York - Associated Visitors Bureau

    Hotel and Visitor Information for Greater New York City. Discover things to do, places to dine and where to spend the night.

  • 13. Shelburne Falls, MA

    If you love hiking, ziplining, music, art and natural beauty all around you, Shelburne Falls, MA is the place. It’s family friendly, fun and fabulous. Shelburne Falls is located on the scenic, historic Mohawk trail in the Berkshire foothills. The Berkshire east ski area in the summer months turns into New England’s largest zip line destination.


    Visit Shelburne Falls, Massachusetts, on the Mohawk Trail - home of the Bridge of Flowers and Glacial Potholes.

  • 14. Ogunquit, ME

    72 miles from Boston 

    The Marginal Way in Ogunquit is famous for it’s stunning views of the ocean and beautiful homes. Walking the Marginal Way is a great way to experience this special place. Make sure you visit the Front Porch for a good old fashioned piano bar sing-a-long. It’s a must-do. There are shows, incredible restaurants, walking paths and shopping. The lobster rolls and sunsets are unmatched.

    2023 ULTIMATE Guide To Ogunquit Maine | Best Things To Do

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  • 15. Gloucester, MA

    39.4 miles from Boston 

    Travel & Leisure declared the tiny North Shore town of Gloucester, MA one of the 12 best places to visit in August. Country star Kenny Chesney has been known to pop into Gloucester from time to time. What is it about Gloucester? It’s the rich history of maritime and fishing. It’s the delicous, fresh seafood, a bustling waterfront, and gorgeous beaches. There’s a lively arts scene, museums, water sporting fun, boating, downtown boutiques, fun bars and great restaurants.

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  • 16. Plymouth, MA

    37 miles from Boston 

    If you haven’t been to America’s Hometown in a minute, you need to revisit. It’s bustling and booming with history,  quaint shops, fantastic dining options (with views, and in town), arts, music and theater. My last visit there I had such a great time antiquing, shopping, dining and just walking around. And that was off-season. Next time I go, I may try one of the culinary tours or wine tasting at Cordage Park.

    See Plymouth | The Official Tourism Site of Plymouth County

    See all that Plymouth County has to offer. See Plymouth explores nearby things to do, lodging, and dining options for you and your family to explore during your visit.

  • 17. Chatham, MA

    87.9 miles from Boston 

    It’s all about the views, here. Chatham is surrounded by water on three sides. Fishing, boating, kayaking, anything on the water is popular. The pristine white sand beaches, the lighthouse, the windmill, golfing and shopping are huge attractions in this pretty-as-a-picture town. In recent years, it’s been known for it’s shark sightings, but there are plenty of whale watch excursions you can check out, or watch seals right from the pier or the coast. The famous Chatham Bars Inn is worth a visit, at least for a drink and the view.

    What to See & Do

    There is so much to do in Chatham! Why do most people come to Chatham for vacation or to live? The Beaches! With miles of pristine white sand, a day at the beach, swimming, stretching with yoga or even surf casting is better than a day in the office.

  • 18. Hampton Beach, NH

    Hot fun in the summertime. It’s happening at Hampton Beach. Entertainment, famiy fun, nightlife, live music, and the old fashioned arcade and casino fun of a summer boardwalk is here. There is never a dull moment on Hampton Beach!

    Vacation Planning

    24th Annual Hampton Beach Master Sand Sculpting Classic






  • 19. Providence, RI

    50 miles from Boston

    Food glorious food. Night life, history, the ocean. It’s all just about an hour away from Boston. Providence is often named one of the best cities for foodies. It’s a city small enough to get around but big enough to have plenty of sparkle. Providence has a flourishing arts community, and it’s rich in history. There are views to be seen, Italian food to be eaten, and live music to experience here. And don’t miss Waterfire Providence. A spectacular display of firey art on the water. It’s a sculpture on the rivers of downtown Providence that began on First Night in 1994 and took off. Walk the riverfront and take in flickering firelight, “the fragrant scent of aromatic wood smoke, the changing silhouettes of the volunteer fire tenders, and the music.” (Wikipedia)

    Providence, RI | Attractions, Things to Do & Events

    Providence, RI hosts a small-town charm with big-city culture and sophistication with museums, attractions and events to keep you constantly on the move.

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