Top 16 Best New England Vacation Destinations

I'm a little partial to Massachusetts because I live there, but it's also the hub of New England, and geographically in the middle. It has some of the best coastlines on the entire east coast, and some great seaside towns to explore. My top picks for destinations to visit in Massachusetts are the following:

Martha's Vineyard: The more accessible large island off the southern coast of Massachusetts, Martha's Vineyard is someplace that you should definitely try to visit while in New England. Not only are some of the best beaches located here, but the views across the island are incredible. Like Nantucket, it has largely maintained its rustic, undeveloped atmosphere. There aren't any big towns, carnivals, or major attractions here other than relaxing and getting away from the mainland, so enjoy!

Cape Cod: This is the place to go during the summer in Massachusetts. There are two ways to get here: fight through the traffic over the bridges, or fly. Most people choose to drive over the Sagamore or Bourne Bridge, one of the two unofficial entryways onto the Cape. Art galleries, restaurants, boating, beaches, whale watches, and scenic drives are some of the best things to do here. If you're looking to experience Cape Cod without the traffic and pedestrian congestion, come here after Labor Day or before the middle of June (though post Memorial Day it is busy). 

Boston: Centrally located in New England, Boston is the commercial epicenter of the six states. What makes Boston unique is its history and neighborhoods. Each has its own flavor with differing architecture, businesses, and appeal. Compare in neighborhoods like the North End, Southie, Back Bay, and Government Center. 

Nantucket: It's hard to get to, but well worth the boat ride (or flight). This island is located east of Martha's Vineyard, south of Chatham. Like The Vineyard, it is rustic, and its greatest appeal is its lack of man-made, flashy, commercial attractions. Nantucket's greatest asset is its ability to relax even the most stressed out visitor with its calming waves, picturesque sand dunes, towering historic lighthouses, and preserved old world feel.

The Berkshires: The Berkshires is a region of western Massachusetts west of the Connecticut River, all the way to the New York State border. This mountainous region is full of small mountainside towns, breathtaking views, art museums, highly rated restaurants, hiking destinations, historic buildings, and botanical gardens. There's a lot to do here, and the scenic drives are amazing, especially in fall. 

Plymouth: South of Boston and north of Cape Cod, the town of Plymouth is located on the South Shore, and has several historic sites worth checking out. The first is Plymouth Rock, where the Mayflower originally landed. The other historic sites in town to check out are the Mayflower II, an exact replica of the ship that the Pilgrims used to get to the New World. Down the street, Plimoth Plantation recreates Pilgrim society in its authentic setting. Don't forget to take a stroll along Plymouth's waterfront area, then head up to Main Street/Court Street, where you can find hundreds of shops, pizzerias, restaurants, and bars to relax at. 

Photo of Mayflower II by joiseyshowaa on flickr, licensed under Creative Commons 2.0.

Connecticut Wine Trail: Who knew that so many wineries existed in Connecticut, or that wine would grow here at all? There are over 20 different wineries located in the state of Connecticut, all across the state. There's a wine trail map that connects the dots between these many wineries. A great way to spend a summers day in southern New England!

Mystic Seaport: Easily accessible via I-95, Mystic Seaport is a short drive over the Rhode Island border into Connecticut. The town, even from I-95, looks impressive. Located within town is the acclaimed Mystic Aquarium. Just around the corner, the Mystic Seaport area is a beautiful place you'll want to stop by take photos and browse the museum. 

Photo of Mystic by Greg Moine, licensed under Creative Commons 2.0.

Bar Harbor/Acadia National Park:  I'm going to resort to a cheesy word like "magical" to describe Acadia, because it is awe inspiring at how beautiful it truly is. It has been stated that the peak of Cadillac Mountain is the first spot you can view sunrise on the eastern coast of North America. The early morning sunsets here are spectacular to see, but the park itself is impressive all around. The beaches are beautiful, the ocean is rough, and the town of Bar Harbor is charming. You can easily make a few days visit out of Bar Harbor and Acadia, so take your time here.

Portland: You'd be surprised how much there is to do in Portland. Ferry and boat expeditions leave from Portland to various points throughout the Maine Coast, including whale watches. The city itself is preserved to keep its early American history intact. There are cobblestone streets, beautiful brick buildings, and great views of Portland Harbor throughout the city. 

Acadia beach photo by Surabhi Dhake, licensed under Creative Commons 2.0.

Route 4: The region along Route 4, for all intents and purposes, will be bunched together into one region. The region between Quechee and Killington is a must-see if you're headed to Vermont. Route 4 is easily found off of I-89 on the New Hampshire border. Be sure to stop at Quechee Gorge before you proceed towards historic Woodstock, Vermont, one of New England's most scenic towns. Further west, you'll find Killington, which can be explored by ski lift, hiking, or car ride. 

Lake Champlain: North of the Route 4 region near Burlington, Lake Champlain is Vermont's largest lake, sharing a border with the state of New York. What makes it so unique is that the lake has beautiful mountain backdrops all around, and the horizon appears to be limitless, just like the ocean in some spots. 

Photo by flickr user Eflon, licensed under Creative Commons 2.0.

Block Island: The most remote of all islands off Southern New England, Block Island has been called "One of the 12 last great places in the Western Hemisphere" by The Nature Conservancy.

Newport: Newport is located on Aquidneck Island, part of Rhode Island. The city of Newport is famous for its historic mansions which dominate the southern part of the city on Bellevue Ave and Ocean Drive, but also for its boat racing, stunning suspension bridge, and the mansion-side Cliffwalk.

Photo right of The Breakers in Newport, by pshutterbug, licensed under Creative Commons 2.0.

Franconia Notch: This is where the former "Man on the Mountain" rocky outcropping was located. It has since crumbled, but the area is just as beautiful as ever. Like many parts of New Hampshire, this is a fun place to visit in all four seasons for its hiking, biking, skiing, shopping, and scenic drives. Be sure to check out "The Flume," a bridged area of mountainous rocky slabs that criss-cross between brooks, streams, and rivers in the middle of the deep woods of Franconia. 

Kancamgus Highway: Arguably the most scenic drive in all of New England during the autumn months, this has spectacular fall foliage which you simply can't miss if you're headed here between September and November. Peak season is usually late September to late October, with early to mid October being the best weeks usually (though they vary annually). This road can be found between Lincoln and North Conway.

Photo of Franconia Notch by icemomo, licensed under Creative Commons 2.0.