Covered bridge in the fall at Devil's Hopyard State Park

The Northeast is one of the most amazing areas in the country. I had the opportunity to live in Massachusetts for many years. I enjoyed many wonderful roadtrips during my time here, exploring quaint coastal cities like Newport and Plymouth and hiking at some of the best preserves and state parks in the country.

In addition to being home to some of the country’s largest cities, the region offers a plethora of outdoor activities due to the heavy forest coverage. Maine and New Hampshire take the first and second positions as the most forested states, while the rest of the Northeast falls within the Top 20. I love that I can be walking around a big city one day and then hitting a gorgeous rustic trail the next.

The ability to quickly travel from urban to rural land and between state to state is definitely a perk. This gives you the opportunity to explore so many different places within a single vacation. From charming coastal villages in New England, to beautiful mountain ranges like the Catskills and White Mountains, to exciting cities like Boston, Philadelphia, & New York City, the region offers a bit of everything for everyone.

1. CliffWalk

Cliffwalk sign in Newport, Rhode Island

CliffWalk is one of the most amazing sights in Rhode Island, an underrated state which doesn’t get nearly as much press as it should. This 3.5 mile walk takes you on a coastal journey past Newport’s historic mansions.

If you think they are grand from the outside, just wait until you explore the inside of these lavish estates. Most impressive, the extravagant Breakers Mansion (once the summer home of the Vanderbilts), is home to a whopping 70 rooms!

This walk is a nice budget friendly alternative (it’s free!) for anyone who doesn’t want to pay to tour the famous mansions. If you visit outside of the busy summer season, the walk takes on an even more relaxing nature.

Also be sure to check out my full guide to exploring beautiful Newport

The Breakers Mansion in Newport, Rhode Island
The Breakers, the largest of the extravagant Newport Mansions.
Cliffwalk photo opp
A gorgeous place for a walk!
40 Stone Steps on Newport's CliffWalk.
A view of the 40 Stone Steps lookout in the distance

2. The beaches of Islesboro, Maine

Islesboro, Maine Beach
A gorgeous beach in Islesboro, Maine.

I had the unique opportunity of living on a gorgeous island off the coast of Maine called Islesboro. Its’ secluded nature and beautiful beaches make it a prime summer vacation destination for big city dwellers from NYC and Boston. Although the year-round population is just under 600 residents (including a few notable celebs like John Travolta), the population soars to several thousand during the beautiful summer months.

The gorgeous 14 mile long island is perfect for long summer bike rides, hunting for seaglass at the many historic public beaches, and enjoying nature from your beautiful vacation rental. A visit to the island will require a ferry ride from Lincolnville, although the ride over itself is quite scenic, with a charming lighthouse waiting to greet you as you arrive. I absolutely loved the scenery from my rental home and I could walk right to a gorgeous beach. I became quite the seaglass collector during this time!

Grindle Point lighthouse in Maine
Grindle Point lighthouse and Sailor’s Museum
Public beach in Islesboro, Maine
On the hunt for seaglass

3. The Freedom Trail

Paul Revere statue in Boston
This statue of Paul Revere is one of the most photographed in the city. It is located in the North End neighborhood, near Old North Church.

Visiting Boston without walking the city’s historic brick-lined Freedom Trail would be a major mistake. Even if you are not at all interested in history, it is worth visiting just to enjoy the city ambiance and gorgeous architecture. For those interested in history, you will have a field day exploring the 16 sights which make up the 3 mile journey into Boston’s past.

The Old South Meeting House on the Freedom Trail
The Old South Meeting House is where plans for the Tea Party were set in place.

There are plenty of fantastic stops along the way including some of the city’s top restaurants. I recommend lunch at Giacomo’s in the North End neighborhood – it’s one of the best Italian restaurants I’ve ever dined at. Their pumpkin tortellini is just amazing. If seafood is more your style, Bell in Hand Tavern is a pretty cool place (it’s actually the oldest tavern in America). We enjoyed some great clam chowder here and a gigantic plate of fried seafood known as the Fisherman’s Platter.

Pumpkin Tortellini at Giacomo's in downtown Boston
The best Pumpkin Tortellini I’ve ever tasted: amazing!
Fishermans Platter at Bell in Hand Tavern in Boston, MA
The Fisherman’s Platter is probably one of the best apps I’ve ever had and I am not even the biggest seafood fan!

Other must do’s include: a tour of the Paul Revere house, an inside look at the beautiful architecture of Old North Church, and a tour of the USS Constitution, to name a few. Above all, be sure to climb to the top of Bunker Hill Monument. While it’s exhausting (you will need to walk 294 steps up to the observing area) after a full day of walking, yet so worth it for the incredible panoramic views of the city.

Paul Revere house in downtown Boston
The Paul Revere house, built back in 1680, is the oldest remaining structure in the city. That’s me enjoying the trail all to myself on a cold, desolate winter day.
Old North Church in downtown Boston
Old North Church is the location from which the famous “One if by land, two if by sea,” slogan originated.
Views of Boston from the top of the Bunker Hill monument
The views of Boston from the top of the Bunker Hill monument are nothing short of amazing!

4. Kaaterskill Falls

Kaaterskill Falls in New York

New York’s tallest waterfall is an amazing 2 tier wonder in the beautiful Catskills Region. I really love this region of the state because there is so much rustic nature to explore. I would say it is an amazing escape for NYC locals looking to hike and enjoy nature for the weekend. I’ve taken numerous trips here from Massachusetts and I love the vibe.

One activity for hikers to check out is the trek to Kaaterskill Falls. At a height of 260 feet, it stands mighty as one of the tallest waterfalls in the state. The hike is both peaceful and scenic, and thankfully short at just a mile. The falls are truly an amazing sight not to be missed. It beats any pricey man-made tourist attraction any day. There are plenty of wonderful photo opportunities here, especially if you visit on a weekday morning.

I recommend staying at one of the charming inns or B&Bs in the area. We stayed at this rustic resort called the Emerson. The setting on Esopus Creek is so gorgeous. They offer both lodge accommodations as well as more rustic cabin themed rooms facing the creek. Amenities include: an on-site spa, a restaurant, and the world’s largest Kaleidoscope.

Beautiful Catskill Mountains in Upstate New York
Beautiful Esopus creek from the Emerson Resort

5. Blue Hills Reservation

A beautiful fall hike through Blue Hills in Boston.
A beautiful fall hike through Blue Hills.

Blue Hills is an enormous hiking oasis just outside of Boston. What I love most about this city is how easily you can get somewhere so rustic without even driving that far. You can also visit the Blue Hill Observatory, home to the oldest weather recording station.

With over 100 trails, the park is amongst the largest you will find so close to a major city. It’s so gorgeous all year-round, with scenic green trees and clear skyline views in the summer months and brisk fall colors in September & October. I love leaf peeping, so this is my favorite time to enjoy a trek on the Skyline trail, a challenging 3 mile loop featuring a great overlook of the city.

Pretty views of the Boston skyline from Elliott Tower
The skyline offers one of the best city views at any park
Colorful views during the fall foliage season at Blue Hills Reservation
Colorful views during the fall foliage season from atop Elliott Tower via the Skyline trail

For all the winter lovers out there, you can enjoy some convenient local skiing at Blue Hill Ski area. It’s no Vermont, but it’s much cheaper and more easily accessible. Tubing is also available for any non skiers who still want to enjoy the snow. Overall, this is a fantastic 4 season destination; so close to the city, yet so far away!