Road trip from Boston

If your everyday surroundings start feeling too mundane, you might hear the road calling to you. A surefire way to change your settings and beat monotony is with a road trip. Getting away by car doesn’t require much planning or money and can be done on a whim, unlike cross-country and overseas travels. Just jump behind the wheel, pick a destination, and start your adventure. Whether you are looking for a day trip or a long weekend, solo or with friends, we’ve put together some exciting seasonal road-trip ideas to help you make the most of your adventure! Now we all know that 2020 is turning out to be a very different year in many respects. It’s hard to know if certain events or festivals will take place this year, but don’t let that stop you from exploring! There is always so much to see, so with or without a planned event, you are free to drive until you feel like stopping.

Summer Road Trip Ideas

Manhattanhenge & 4th of July in NYC

New York won’t host formal events in Summer 2020, but that doesn’t mean you should exclude NYC from your road-trip options. In fact, with the possibility of less tourists, this could be the best time to visit. As of early June, the Macy’s 4th of July Fireworks are still set to go on, and you may get to see them without the usual crowds. Manhattanhenge—a phenomenon that happens only twice a year, in late May and mid-July—will certainly occur, and you can be right there to witness it. The Big Apple is only 215 miles (346 km) from Boston, or just 3 hours and 45 minutes. This makes for a spectacular and exciting day trip if you are up for the challenge and want to avoid staying in a hotel.

Puffins near Bristol, Maine

The beautiful coast of New England is well worth your driving time, especially in summer when nature abounds. We recommend exploring the islands off of Maine’s coast which host thousands of puffins during summer months. Eastern Egg Rock is a popular choice close to Boston and just 6 miles (10 km) off the shore. This scenic rocky island is only 7 acres (3 ha), so you are sure to see plenty of birds. Bring binoculars in order to take in every feature of the tiny but mighty puffins! Hardy Boats Cruises depart from New Harbor in Bristol, which is 175 miles (282 km) and just 3 hours away from Boston. The tours are due to reopen on June 20th, 2020, and run through late August.

Fireflies at Chaffey's Lock, near Ottawa | River surfing in Montreal

And last, don’t forget about neighboring Canada. To escape hot and humid days in June and July, venture to Chaffey's Lock, a lake area south of Ottawa, and watch for fireflies at twilight. The driving distance is about 408 miles (657 km), and one-way travel time is around 7 hours. A bit of a shorter drive at 308 miles (496 km) from Boston, or just under 5 hours, Montreal is a great candidate for your road-trip wanderings. Summer is a great season to learn river surfing on the St. Lawrence River, just a stone's throw from the downtown. The thrill-seekers will surely appreciate this extraordinary experience.

Get on the Road This Fall

Indian summer & migrating snow geese in Victoriaville, Quebec

Indian summer (mid-September to late October) is prime time to hit the road to south-central Quebec. Its countless maple trees turn this area into a fairyland of colors. The town of Victoriaville on the Nicolet River, 311 miles (501 km) north of Boston, is an ideal destination. This scenic drive will take around 5 hours and be well worth it. Take your time to appreciate the fascinating landscapes and breathtaking fall foliage. If you’re lucky, you will catch snow geese in their fall migration. For the best chance to see them, get up before the sunrise, as the birds gather near the river in great numbers early in the morning. Sightings occur within Victoriaville, but Baie-du-Febvre at Lac-Saint-Pierre is also a popular spot, and is just one hour from Victoriaville.

The Big E in West Springfield, Massachusetts

You don’t have to leave the state to attend the biggest fair on the East Coast and the largest agricultural event in New England. The Big E takes place in West Springfield, Massachusetts. Only 92 miles (148 km) northwest of Boston—about an hour and 40 minutes—West Springfield is perfect for a one-day road trip!

Sea Witch Festival on Rehoboth Beach, Delaware

If you love Halloween, head to Rehoboth Beach, Delaware. In late October this Atlantic Coast town welcomes hundreds of witches, monsters, and various creatures at the Sea Witch Festival. Located 424 miles (682 km) southwest of Boston, the approximate driving time is 7 hours, but you might want to make a stop in New York City, which is roughly halfway, or check out to Philly which also lies en route.

Macy's Thanksgiving Day Parade in NYC

And finally, fall is a fantastic time for a road trip to the Big Apple, which boasts many iconic events. Opt for the Macy's Thanksgiving Day Parade in late November. We hope that Covid-19 won't hinder either of these events.

Get Away This Winter

Rockefeller Center Christmas Tree in NYC

Remember that scene in Home Alone 2 when McCauley Culkin made his Christmas wishes in Rockefeller Center? Place yourself in the same magical spot and catch the Christmas Tree lighting ceremony (right after Thanksgiving) along with live entertainment. And if you can’t make the tree lighting, come anytime during New York’s spectacular holiday season. The tree will be on display until early January. And don’t hesitate to make a wish! (Boston–NYC driving distance: 215 miles (346 km) or 3 hours and 45 minutes).

Philadelphia Mummers Parade

On New Year’s Day, we suggest visiting the capital city of Pennsylvania. You’ll see the Philadelphia Mummers Parade, a fun and unique street extravaganza that resembles a carnival. This event is known as the state's most popular and widely-visited attraction and is possibly the country's oldest folklore festival. Philly is located 307 miles (494 km) or 5 hours southwest of Boston, and 94 miles (151 km), or 1 hour and 45 minutes, from NYC.

Winterlude & Rideau Canal Ice Rink in Ottawa

Let’s shift the direction to Canada. We strongly recommend visiting Ottawa in January and February for the opportunity to skate along the Rideau Canal. Known as the largest naturally frozen ice rink in the world, it stretches for about 5 miles (8 km). In addition, for a few weeks in February, the city hosts a trendy winter festival called Winterlude, which is fully-packed with seasonal fun. Ottawa is located 435 miles (700 km) northwest of Boston. The driving time is approximately 7 hours.

Quebec Winter Festival

Southern Quebec proves that Canadians are well versed in celebrating winter. The famed Quebec Winter Festival is a great reason to plan a road trip to Quebec City, 397 miles (639 km) or 6 hours and 20 minutes from Boston. The festival is labeled the world’s biggest snow event, and its host-city—the capital of snow. The festivities take place almost simultaneously with Ottawa’s Winterlude, so put both on your agenda for a splendid long-weekend road trip. The distance between Quebec City and Ottawa is 276 miles (444 km), or a 4 hour and 30 minutes drive.

Montreal Nuit Blanche

Another winter destination is Montreal, especially during the famous Nuit Blanche. This sleepless night occurs in late February. The celebration begins at 5 pm and ends at 3 am! From Boston, Montreal is 307 miles (494 km), and the driving time is about 5 hours.

Treat Yourself to a Spring Road Trip

St. Patrick's Day Parade & Manhattanhenge in NYC

We can’t stop directing you to NYC since it's worth visiting any time of year. There is always more to see! In March, the Big Apple hosts the world’s biggest St. Patrick's Day Parade. Give yourself time and pick your spot along 5th Avenue to ensure a good view of 150,000 green marchers. The procession starts at 11 am, and the 215-mile (346-km) drive from Boston is roughly 3 hours and 45 minutes. Fast forward a few weeks, and don’t miss the stunning urban sunset, aka Manhattanhenge, observed in NYC in late May.

Maine Flower Show in Portland

Springtime is all about flowers, which makes Portland, Maine, another must-do seasonal road-trip destination. In late March, Thompson’s Point hosts the well-known Maine Flower Show, an enormous celebration of gardening and horticulture. A scenic 107-mile (172-km) drive along Maine’s coast can be as delightful as the floral exhibitions. Expect circa 1 hour and 50 minutes of driving time.

Maryland Film Festival in Baltimore

In late April and early May, we suggest a road trip to Baltimore, Maryland. This road trip route from Boston is designed primarily for cinephiles, as Baltimore hosts the Maryland Film Festival. Venues usually include the Parkway Theatre, the Charles Theater, Station North Arts, Maryland Institute College of Art (MICA), the Baltimore Museum of Art, the Walters Art Museum, and others. The city is located 404 miles (650 km) southwest of Boston. The journey will take around 6 hours and 20 minutes, excluding any breaks. But you may want to stop by two beautiful cities en route—NYC and Philly.

Cherry blossoms in Montreal | Canadian Tulip Festival in Ottawa

To round up the spring road trip routes, we suggest more flowers and blossoms. Early May is a pretty time to head to Montreal, 307 miles (494 km) from Boston, a 5-hour journey. The city is beautiful at this time of year, owing to cherry blossoms that turn countless public places pink. Another option is Ottawa, 435 miles (700 km) from Boston, a 7-hour journey. In mid-May, this city hosts the Canadian Tulip Festival. With a display of 250,000 flowers in Commissioners Park, it’s among the largest tulip celebrations in the world.