New England is one of the USA's most beautiful regions. With adorable coastal towns, homey mountain villages, and charming lakeside settlements, New England is the perfect place for a USA getaway. Growing up in Boston, I was lucky enough to visit tons of small towns in New England. These 11 are my all time favorites that I keep going back to. Read on to discover the 11 cutest towns in New England - From a Local.

This post is all about the 11 cutest towns in New England - From a Local.

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1. Portsmouth, New Hampshire

Located just an hour north of Boston, Portsmouth, New Hampshire is the quintessential cozy, New England town. This charming New Hampshire town is home to adorable boutiques, amazing seafood restaurants, coastal views, and more. Portsmouth is also a historic town, much like the rest of New England. So you will find colonial buildings and interesting museums in this small town.

🌊Read Next - A Complete Guide To Portsmouth, New Hampshire

Top 10 Things To Do In Portsmouth, New Hampshire

1. Explore Market Street
2. Visit Strawbery Banke Museum
3. USS Albacore Museum
4. Take a Stroll In Prescott Park
5. See a Show At The Music Hall
6. Moffatt-Ladd House & Garden
7. Do a Day Trip To Maine
8. Go To The Beach
9. Have a Seafood Feast
10. Shop at The Unique Boutiques

🛎️Our Favorite Portsmouth Hotel - The Hotel Portsmouth 

2. Bar Harbor, Maine

Located right next to the stunning Acadia National Park, Bar Harbor, Maine is an adorable seaside town on Maine's rocky coast. Bar Harbor is the perfect place for a New England getaway with its picturesque beaches, top notch seafood restaurants, and niche boutiques.

Top 10 Things To Do In Bar Harbor, Maine

1. Stop By The Abbe Museum
2. Explore Downtown Bar Harbor
3. Try Maine Lobster
4. Visit One Of The Nearby Islands
5. Stop By Bill & Ben's Chocolate Shop
6. Go Whale Watching
7. Visit Acadia National Park
8. See Mount Rainier
9. Go To The Beach
10. Stay at The Bar Harbor Inn

🛎️Our Favorite Bar Harbor Hotel - The Bar Harbor Inn

3. Newport, Rhode Island

Newport has one of the wealthiest zip codes in the country. Most well known for the 11 Newport Mansions, Newport, Rhode Island is easily one of the cutest towns in New England. While in Newport visit one of the many beaches, explore downtown, shop at the preppy boutiques, and visit the Newport Mansions!

🎾Read Next - A Complete Guide To Newport, Rhode Island

Top 10 Things To Do In Newport, Rhode Island

1. See Ocean Drive
2. The 11 Mansions
3. The Tennis Hall of Fame
4. the Newport Cliff Walk
5. The Beach
6. Stop By One of the Legendary Breweries
7. Have a Go at Surfing
8. Do The Bike Path
9. Try The Local Seafood
10. Go To The Newport Car Museum

🛎️Our Favorite Newport Hotel - The Vanderbilt Hotel

4. Stowe, Vermont

Stowe is an enchanting town in the northern part of Vermont that truly becomes a wonderland in the winter. This charming New England Town is home to the highest peak in Vermont. Skiers and Snowboarders flock here every winter to conquer Stowe Mountain.

Stowe is also known for its luxurious Stowe Mountain Resort. I loved visiting Stowe as a kid. Stowe Mountain Resort reminds me of a town in the Swiss Alps because of its remoteness and European flare.

Top 10 Things To Do In Stowe, Vermont

1. Visit Stowe Mountain Resort
2. Go Skiing or Snowboarding
3. Do a Hike
4. Visit Mount Mansfield
5. Explore Downtown Stowe
6. Try Vermont Maple Syrup
7. Visit The Ben & Jerry's Factory
8. Smugglers Notch State Park
9. Visit Woodstock
10. Go on the Iconic Stowe Gondola

🛎️Our Favorite Stowe Hotel - Stowe Mountain Resort

5. Provincetown, Massachusetts

Provincetown is an adorable seaside town located at the tip of the Cape. This charming village is known for its art scene, gay pride, stunning beaches, and adorable coastal hotels. Provincetown is easily one of the best towns on Cape Cod.

🦞Read Next - A Complete Guide To Provincetown, Massachusetts

Top 10 Things To Do In Provincetown, Massachusetts

1. Commercial Street
2. The Lobster Pot
3. Provincetown Beaches
4. Visit The Art Galleries
5. Walk The Dunes Shacks Trail
6. Old Harbor Life-Saving Station Museum
7. Explore More of The Cape and Islands
8. Stay At The White Porch Inn
9. Herring Cove Beach
10. Try The Local Seafood

🛎️Our Favorite Provincetown Hotel - White Porch Inn

6. Manchester-By-The-Sea, Massachusetts

I grew up just a few towns over from Manchester-By-The-Sea and it was easily one of my favorite places to go growing up. The small seaside village is located just north of Boston in Cape Ann. The lovely coastal town is home to gorgeous beaches, amazing seafood restaurants, and adorable boutiques. Manchester-By-The-Sea is a great place for a day trip from Boston or a beach vacation.

🛶Read Next - A Perfect Guide To Manchester-By-The-Sea

Top 10 Things To Do In Manchester-By-The-Sea

1. Visit Singing Beach
2. Masconomo Park
3. Go Shopping In Downtown
4. Lobster Cove Beach
5. Go Fishing or Have a Boat Day
6. Try The Local Seafood
7. Visit The Neighboring Towns
8. Have A Go At Surfing
9. Have Ice Cream at Captain Dusty's
10. Visit Ram Island

🛎️Our Favorite Manchester-By-The-Sea Hotel - Rental In Manchester-By-The-Sea

7. Rockport, Massachusetts

Located just north of Manchester-By-The-Sea is Rockport, a another stunning coastal town. This charming town is a bit more lively and bigger than Manchester-By-The-Sea. With cute cafes, adorable shops, and stunning beaches, Rockport is an underrated town in Massachusetts.

Top 10 Things To Do In Rockport, Massachusetts

1. Explore Halibut Point State Park
2. Walk Down Bearskin Neck Road
3. Visit The Rockport Harbor
4. Front Beach
5. Go Whale Watching
6. Thacher Island
7. Hammond Castle Museum
8. The Art of David Arsenault
9. Motif #1
10. Eat Lobsta Rolls

🛎️Our Favorite Rockport Hotel - The Addison Choate Inn

8. Martha's Vineyard, Massachusetts

Martha's Vineyard is a stunning Island off the coast of Cape Cod and next to the famous Nantucket Island. The Vineyard is a bit more low key and affordable than the nearby Nantucket, but it has that same preppy island vibe. Martha's Vineyard is made up of six towns (Aquinnah, Chilmark, Oak Bluffs, Edgartown, Vineyard Haven, and West Tisbury).

All of there towns are wonderful, but my personal favorite is Edgartown.

🦭Read Next - A Complete Guide To Martha's Vineyard

Top 10 Things To Do In Martha's Vineyard, Massachusetts

1. Martha's Vineyard Gingerbread Houses
2. Aquinnah Cliffs Overlook
3. Explore downtown Oak Bluffs
4. Go To The Beach
5. Jump Off Of Jaws Bridge
6. Chappaquiddick Island
7. Explore Edgartown
8. See The Edgartown Lighthouse
9. Try The Local Food
10. Have a Boat Day

🛎️Our Favorite Martha's Vineyard Hotel - Harbor View Hotel

9. Conway, New Hampshire

Conway is a tiny town in the heart of the White Mountains in New Hampshire. While there is not much going on in the small town, there is so much natural beauty surrounding it. During the winter you can go skiing, snowmobiling, or snowshoeing and in the summer you can hike through the stunning mountain range.

Top 10 Things To Do In Conway, New Hampshire

1. Go Snowmobiling
2. Go Hiking
3. Go Skiing
4. Explore Echo State Park
5. See Diana's Baths
6. See The Historic Conway Train
7. Stay at or visit The Mount Washington Resort
8. Visit Santa's Village
9. Explore Downtown
10. Try The Maple Syrup

🛎️Our Favorite Conway Hotel - The White Mountain Resort

10. Mystic, Connecticut

Mystic, Connecticut is a charming town located in the southern part of Connecticut. Mystic is most well known for its adorable downtown area, close proximity to the beach, and historical buildings. The best time to visit Mystic is over the summer or fall.

🍕Read Next - The Best Mystic, Connecticut Travel Guide

Top 10 Things To Do In Mystic, Connecticut

1. Eat At The Iconic Mystic Pizza
2. Denison Homestead
3. Shopping In Downtown Mystic
4. Mystic Seaport Museum
5. Old Mystic Village
6. Mystic Museum of Art
7. Denison Pequotsepos Nature Center
8. Take a Day Trip To Newport, Rhode Island
9. Mystic Seaport Museum
10. Mystic Ghost Tour

🛎️Our Favorite Mystic Hotel - The Whaler's Inn

11. Chatham, Massachusetts

Chatham is one of the best towns on Cape Cod and easily one of the cutest towns in New England. Located on the elbow of the Cape, Chatham is home to picturesque beaches, an adorable downtown area, lovely hotels, and charming eateries. Chatham is truly the perfect town for a Cape Cod Vacation. It is a bit pricey, so if you are looking for a more affordable town you could checkout the neighboring Harwich.

🦈Read Next - What To Do In Chatham, Massachusetts

Top 10 Things To Do In Chatham, Massachusetts

1. Chatham Lighthouse
2. Monomoy
3. Downtown Chatham
4. The Candy Manor
5. Go To The Beach
6. Oyster Pond
7. Chatham Pier Fish Market
8. Visit Shore Road
9. Visit The Chatham Shark Center
10. Take a Day Trip

🛎️Our Favorite Hotel In Chatham, MA - Chatham Bars Inn 

11 Cutest Towns In New England - From a Local Wrap Up

Growing up in New England was such a treat. While this guide didn't mention some of the more popular New England towns like Salem and Woodstock, but these 11 are my all time favorite. We hope that these 11 cutest towns in New England help you plan the best trip to the incredible region. If you liked this post we think that you will love our guide to the Best Mother-Daughter Trips To Take In The USA or The 13 Most European Cities In America.

Happy Travels,

Daisy

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