Events & Festivals

Check out our events calendar

Exciting things are always happening here in Portland, and our hotel places you conveniently near them all. From baseball games to festivals and concerts, the city’s event schedule offers fun and interesting ways for you and your family to discover and enjoy during your time here. Peruse our list below for a sampling of area events worth experiencing.

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  • Martinis for Mutts

    It's our fourth annual Martinis for Mutts, the best yappy hour in town! Hosted by the Portland Regency Hotel & Spa and HappyME , this event is always a barking good time. Tickets for this…
    read more
  • Mother's Day Brunch in our dining room

    Come celebrate Mom with us.  We will be serving Brunch in our dining from 7am until 2pm and Dinner from 5pm until 8pm. Menu
    read more
  • Easter Buffet

    Join the Easter Bunny for our Easter Buffet served 10am-2pm in the Atlantic Room.  Reservations 207-774-4200 

    read more
  • Maine Restaurant Week

    Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

    read more
  • Valentine's Day in our Dining Room

    Twenty Milk Street welcomes diners with warm, intimate décor, punctuated by softly lit chandeliers and a lovely brick fireplace. Our Valentine's Menu will be served Saturday, February 13th 5-9:30pm…
    read more
  • Jim Ciampi Trio in our Dining Room

    Twenty Milk Street Restaurant, in the Portland Regency Hotel and Spa, is proud to present the “Jim Ciampi Trio”. Performing Thursdays starting February 11th. The “Jim Ciampi Trio” will be preforming…
    read more
  • New Year's Eve Gala

    The Portland Regency Hotel & Spa cordially invites you to our 2015 New Year’s Eve Gala! Ring in the new year dressed to the nines and join us for an evening to remember! Mingle as you’re serenaded…
    read more
  • Beach to Beacon 10K

    The Beach to Beacon 10K was founded by 1984 Olympic Marathon Gold Medalist and Cape Elizabeth native Joan Benoit Samuelson. The 2015 race drew over 6,000 athletes, with proceeds from the event benefiting…
    read more
  • Tri for a Cure

    Headed by the Maine Cancer Foundation, this women’s only triathlon raises valuable funds to provide much-needed support to the MCF’s efforts, and to continue the battle against cancer.

    read more
  • Yarmouth Clam Festival

    For over 50 years, this festival has billed itself as a “Maine summertime tradition”; it offers fireworks, a parade, food and live entertainment, and plenty of terrific activities for the kids. And admission…
    read more
  • Old Port Festival

    Start summer in style at this three-day festival here in the Old Port, with music, dance, food, kids’ events, and much more. It’s a wonderful way to get a sense of the city’s personality and vibe
    read more
  • First Friday Art Walk

    This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor…
    read more
  • Maine Brewers Festival

    Celebrate your love of craft beer at this one-day extravaganza, hosted at the nearby Portland Expo. Nearly 20 different brewers will be exhibiting; enjoy delicious food and live entertainment while you…
    read more
  • Harvest on the Harbor

    Foodies, wine connoisseurs, and those looking to sample the wares of some of Maine’s best chefs should plan to visit this four-day festival, located right here in the Old Port. The festival boasts a range…
    read more
21
Oct

Harvest on the Harbor

Foodies, wine connoisseurs, and those looking to sample the wares of some of Maine’s best chefs should plan to visit this four-day festival, located right here in the Old Port. The festival boasts a range of events, from informal wine tastings to fancy galas; local musicians are on hand to keep you entertained while you eat and drink

22
Oct

Harvest on the Harbor

Foodies, wine connoisseurs, and those looking to sample the wares of some of Maine’s best chefs should plan to visit this four-day festival, located right here in the Old Port. The festival boasts a range of events, from informal wine tastings to fancy galas; local musicians are on hand to keep you entertained while you eat and drink

23
Oct

Harvest on the Harbor

Foodies, wine connoisseurs, and those looking to sample the wares of some of Maine’s best chefs should plan to visit this four-day festival, located right here in the Old Port. The festival boasts a range of events, from informal wine tastings to fancy galas; local musicians are on hand to keep you entertained while you eat and drink

24
Oct

Harvest on the Harbor

Foodies, wine connoisseurs, and those looking to sample the wares of some of Maine’s best chefs should plan to visit this four-day festival, located right here in the Old Port. The festival boasts a range of events, from informal wine tastings to fancy galas; local musicians are on hand to keep you entertained while you eat and drink

25
Oct

Harvest on the Harbor

Foodies, wine connoisseurs, and those looking to sample the wares of some of Maine’s best chefs should plan to visit this four-day festival, located right here in the Old Port. The festival boasts a range of events, from informal wine tastings to fancy galas; local musicians are on hand to keep you entertained while you eat and drink

06
Nov

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

07
Nov

Maine Brewers Festival

Celebrate your love of craft beer at this one-day extravaganza, hosted at the nearby Portland Expo. Nearly 20 different brewers will be exhibiting; enjoy delicious food and live entertainment while you taste some of the country’s best microbrews.

04
Dec

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

31
Dec

New Year's Eve Gala

The Portland Regency Hotel & Spa cordially invites you to our 2015 New Year’s Eve Gala! Ring in the new year dressed to the nines and join us for an evening to remember!

Mingle as you’re serenaded by live piano jazz from Portland’s own Jim Ciampi (8pm-9:00pm).

Satisfy your cravings with an array of Hors d’oeuvres and desserts

Revel in specialty cocktails, local brews & wine at our cash bar.

Dance the night away to a live 7-piece band starting at 9:30pm

Join in on the countdown and toast to 2016!...

Tickets are $85.00 for one or $160 for two!   Gala Tickets

Overnight packages are available, please call 207-774-4200 for more information!
 
 
11
Feb

Jim Ciampi Trio in our Dining Room

Twenty Milk Street Restaurant, in the Portland Regency Hotel and Spa, is proud to present the “Jim Ciampi Trio”. Performing Thursdays starting February 11th.

The “Jim Ciampi Trio” will be preforming a sophisticated backdrop to cocktails and dinner atmosphere. Featuring sax, percussion and piano with light vocals, the trio voyages through jazz, contemporary, pop and the American songbook. Featuring tunes from yesterday and not so long ago.

Join us in our for cocktails, lite fare, or dinner. Sit by the fire, relax and listen to great live music with Jim and Friends. Valentine’s Day is just around the corner, start early with dinner and entertainment in one of Portland’s most romantic restaurants!

Time: 5:30-8:00 p.m. Performance dates: Thursdays, February 11th, 25th and March 10th and 24th.

20 Milk Street, Portland, 207-774-4200 - Complimentary Valet Parking

13
Feb

Valentine's Day in our Dining Room

Twenty Milk Street welcomes diners with warm, intimate décor, punctuated by softly lit chandeliers and a lovely brick fireplace. Our Valentine's Menu will be served Saturday, February 13th 5-9:30pm and Sunday, February 14th 5-9:00pm

Reservations are strongly suggested Valentine's weekend.

14
Feb

Valentine's Day in our Dining Room

Twenty Milk Street welcomes diners with warm, intimate décor, punctuated by softly lit chandeliers and a lovely brick fireplace. Our Valentine's Menu will be served Saturday, February 13th 5-9:30pm and Sunday, February 14th 5-9:00pm

Reservations are strongly suggested Valentine's weekend.

25
Feb

Jim Ciampi Trio in our Dining Room

Twenty Milk Street Restaurant, in the Portland Regency Hotel and Spa, is proud to present the “Jim Ciampi Trio”. Performing Thursdays starting February 11th.

The “Jim Ciampi Trio” will be preforming a sophisticated backdrop to cocktails and dinner atmosphere. Featuring sax, percussion and piano with light vocals, the trio voyages through jazz, contemporary, pop and the American songbook. Featuring tunes from yesterday and not so long ago.

Join us in our for cocktails, lite fare, or dinner. Sit by the fire, relax and listen to great live music with Jim and Friends. Valentine’s Day is just around the corner, start early with dinner and entertainment in one of Portland’s most romantic restaurants!

Time: 5:30-8:00 p.m. Performance dates: Thursdays, February 11th, 25th and March 10th and 24th.

20 Milk Street, Portland, 207-774-4200 - Complimentary Valet Parking

01
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

02
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

03
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

04
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

05
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

06
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

07
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

08
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

09
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

10
Mar

Jim Ciampi Trio in our Dining Room

Twenty Milk Street Restaurant, in the Portland Regency Hotel and Spa, is proud to present the “Jim Ciampi Trio”. Performing Thursdays starting February 11th.

The “Jim Ciampi Trio” will be preforming a sophisticated backdrop to cocktails and dinner atmosphere. Featuring sax, percussion and piano with light vocals, the trio voyages through jazz, contemporary, pop and the American songbook. Featuring tunes from yesterday and not so long ago.

Join us in our for cocktails, lite fare, or dinner. Sit by the fire, relax and listen to great live music with Jim and Friends. Valentine’s Day is just around the corner, start early with dinner and entertainment in one of Portland’s most romantic restaurants!

Time: 5:30-8:00 p.m. Performance dates: Thursdays, February 11th, 25th and March 10th and 24th.

20 Milk Street, Portland, 207-774-4200 - Complimentary Valet Parking

11
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

12
Mar

Maine Restaurant Week

Join us in our dining room March 1st - 12th.  Our Restaurant Week menu is priced at $35 for an appetizer, entree and dessert. 

27
Mar

Easter Buffet

Join the Easter Bunny for our Easter Buffet served 10am-2pm in the Atlantic Room.  Reservations 207-774-4200 

01
Apr

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

06
May

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

08
May

Mother's Day Brunch in our dining room

Come celebrate Mom with us.  We will be serving Brunch in our dining from 7am until 2pm and Dinner from 5pm until 8pm. Menu

03
Jun

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

12
Jun

Old Port Festival

Start summer in style at this three-day festival here in the Old Port, with music, dance, food, kids’ events, and much more. It’s a wonderful way to get a sense of the city’s personality and vibe

01
Jul

Old Port Festival

Start summer in style at this three-day festival here in the Old Port, with music, dance, food, kids’ events, and much more. It’s a wonderful way to get a sense of the city’s personality and vibe

15
Jul

Yarmouth Clam Festival

For over 50 years, this festival has billed itself as a “Maine summertime tradition”; it offers fireworks, a parade, food and live entertainment, and plenty of terrific activities for the kids. And admission is free to the public.

16
Jul

Yarmouth Clam Festival

For over 50 years, this festival has billed itself as a “Maine summertime tradition”; it offers fireworks, a parade, food and live entertainment, and plenty of terrific activities for the kids. And admission is free to the public.

17
Jul

Tri for a Cure

Headed by the Maine Cancer Foundation, this women’s only triathlon raises valuable funds to provide much-needed support to the MCF’s efforts, and to continue the battle against cancer.

17
Jul

Yarmouth Clam Festival

For over 50 years, this festival has billed itself as a “Maine summertime tradition”; it offers fireworks, a parade, food and live entertainment, and plenty of terrific activities for the kids. And admission is free to the public.

05
Aug

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

06
Aug

Beach to Beacon 10K

The Beach to Beacon 10K was founded by 1984 Olympic Marathon Gold Medalist and Cape Elizabeth native Joan Benoit Samuelson. The 2015 race drew over 6,000 athletes, with proceeds from the event benefiting the Good Shepherd Food Bank.

24
Aug

Martinis for Mutts

It's our fourth annual Martinis for Mutts, the best yappy hour in town! Hosted by the Portland Regency Hotel & Spa and HappyME, this event is always a barking good time. Tickets for this sell-out event go on sale Thursday, July 21st.  Tickets are on-line sales through the Animal Refuge League of Greater Portland.   Join us Wednesday, August 24th from 5:30-7:30pm, rain date August 25th. www.arlgp.org.

02
Sep

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

07
Oct

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

04
Nov

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.

02
Dec

First Friday Art Walk

This fantastic free cultural event allows you to explore Portland’s thriving cultural scene on a weekly basis. Stroll the galleries and museums within the city’s downtown area, munch on treats from outdoor vendors, watch live entertainment, and purchase work from local artists.